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1 Supporting Information Bifunctional Silver(I) Complex-Catalyzed CO 2 Conversion at Ambient Conditions: Synthesis of a-methylene Cyclic Carbonates and Derivatives Qing-Wen Song, [a] Wei-Qiang Chen, [b] Ran Ma, [a] Ao Yu, [b] Qiu-Yue Li, [a] Yao Chang, [a] and Liang-Nian He* [a] cssc_ _sm_miscellaneous_information.pdf
2 Table of Contents 1. General Experimental Methods... S CO 2 Labeling Experiment....S5 3. DFT Calculation...S8 4. Characterization Data for Substrates and Products... S12 5. NMR Spectral Copies of the Substrates and Products... S18 S1
3 1. General Experimental Methods General analytic methods. 1 H NMR spectra was recorded on 400 MHz spectrometers using CDCl 3 or DMSO-d 6 as solvent referenced to CDCl 3 (7.26 ppm) or DMSO-d 6 (2.50 ppm). 13 C NMR was recorded at MHz in CDCl 3 (77.00 ppm) or DMSO-d 6 (39.52 ppm). 31 P NMR was recorded at MHz in DMSO-d 6. Multiplets were assigned as singlet, doublet, triplet, doublet of doublet, multiplet and broad singlet. FT-IR was recorded on a Bruker Tensor27 FT-IR spectrophotometer with KBr pellets. High resolution mass spectrometry was conducted using a Varian 7.0 T FTICR-MS by ESI technique. GC analyses were performed on Shimadzu GC-2014, equipped with a capillary column (RTX-17, 30 m 0.25 μm) using a flame ionization detector. Mass spectra were recorded on a Shimadzu GCMS-QP2010 equipped with a RTX-5MS capillary column at an ionization voltage of 70 ev. The data are given as mass units per charge (m/z). Materials. Unless otherwise noted, carbon dioxide (99.99%), 13 C-labeled carbon dioxide (purity >99.9%, 13 C 99%, 18 O <1%), commercially available propargylic alcohols. All starting materials were obtained from TCI, Aladdin or Alfa Aesar and used as received. All reactions were carried out without any special precautions against air. Procedure for the synthesis of propargylic alcohols 1h and 1i. [1] After anhydrous acetone or cyclohexanone (20 mmol), ethynylbenzene (20 mmol), and potassium t-butoxide (20 mmol) were well-mixed with agate mortar and pestle, the mixture was kept at room temperature for 20 min. The reaction product was mixed with 10% aqueous sodium chloride, filtered, washed with water, and dried to give as colorless crystal. Synthesis of [(Ph 3 P) 4 Ag 2 ](CO 3 ). 2H 2 O and [(Ph 3 P) 2 Ag(HCO 3 )] [2] [(Ph 3 P) 4 Ag 2 (CO 3 )] 2H 2 O. Disilver(I) carbonate (0.138 g, 0.5 mmol) was added to a solution of triphenylphosphine (0.787 g, 3.0 mmol) dissolved in warm acetonitrile (15 ml) and the mixture was stirred at ambient temperature in an open flask for 3 h. Further acetonitrile was added and the mixture was gently heated to ca. 60 o C to dissolve the solid product. The resulting solution was filtered while hot to remove the black residue (fast heat or higher temperature leads to more black residue), and colourless crystals formed upon slow cooling of the filtrate. The product was collected by vacuum filtration. Yield 0.29 g (86%). 1 H NMR (400 MHz, DMSO-d 6 ) (m, 12 H), (m, 48 H), 3.33 (H 2 O) ppm. 13 C NMR (100.6 MHz, DMSO-d 6 ) 133.9, 133.8, 132.5, 132.3, 129.7, 128.7, ppm. 31 P NMR (161.9 MHz, DMSO-d 6 ) 6.57 ppm. ESI (4.8 kv): m/z and [(Ph 3 P) 2 Ag + ]. S2
4 [(Ph 3 P) 2 Ag(HCO 3 )]. To a boiling solution of triphenylphosphine (1.574 g, 6.0 mmol) in ethanol (30 ml) was added, with stirring, a hot solution of silver nitrate (0.510 g, 3.0 mmol) in water (5 ml). The resulting hot solution was immediately added, with rapid stirring, to a solution of sodium bicarbonate (1.05 g, 12.5 mmol) in water (30 ml) at ambient temperature. Then, the mixture was stirred until cool and the product was collected by vacuum filtration and washed with 1:1 EtOH/H 2 O. Yield 1.91 g (92%). A portion of this product (1.0 g) was dissolved in acetonitrile by stirring and heating to 75 C in a water bath. The resulting solution was filtered, and colourless crystals formed upon cooling of the filtrate in an open beaker and evaporation of about half of the solvent. Colourless crystals of the product were collected and dried on a piece of filter paper. 1 H NMR (400 MHz, DMSO-d 6 ) (m, 6 H), (m, 12 H), (m, 12 H) ppm. 13 C NMR (100.6 MHz, DMSO-d 6 ) 133.4, 133.2, 131.8, 131.6, 130.6, 129.1, ppm. 31 P NMR (161.9 MHz, DMSO-d 6 ) 7.61 ppm. ESI (4.8 kv): m/z and [(Ph 3 P) 2 Ag + ]. Table S1. Investigation of molar ratio of PPh 3 to [Ag + ]. [a] 1. Entry PPh 3 /[Ag + ] Yield [%] [b] [a] Reaction conditions: 1a (0.421 g, 5 mmol), Ag 2 CO 3 (6.9 mg, 0.5 mol%), CO 2 balloon, 1 h, 25 o C. [b] Yield was determined by GC with biphenyl as the internal standard. S3
5 1 H NMR (a) 3,4,5 2,6 (b) 4 2,3,5,6 (c) 4 2,3,5,6 13 C NMR 2,6 (a) 1 3,4,5 (b) 2,6 1 3,4,5 (c) 2,6 1 3,4,5 31 P NMR (a) (b) (c) Figure S1. 1 H, 13 C and 31 P NMR (400 MHz, DMSO-d 6 ) charts for (a) PPh 3, (b) the precipitate isolated from the reaction mixture [reaction conditions: 1a (0.211 g, 2.5 mmol), Ag 2 CO 3 (3.5 mg, 0.5 mol%), PPh 3 (26.2 mg, 2.0 mol%), 1 bar CO 2 at 25 o C for 2 h] after the reaction completion, (c) the prepared [(Ph 3 P) 2 Ag] 2 CO 3 according to ref. [2]. In the 1 H NMR, the downfield shift of the CH (C 2, C 4, C 6 : from δ = 7.38 to 7.47 ppm of C 4, from δ= 7.24 to 7.34 ppm of C 2 and C 6 ) is in accord with values of freshly-prepared [(Ph 3 P) 2 Ag] 2 CO. 3 2H 2 O. In the 13 C NMR spectra, the upfield shift of the carbon signal from δ = to ppm (C 1 ) is in agreement with the formation of the [(Ph 3 P) 2 Ag] 2 CO 3 species. Noticeably, 31 P NMR spectra showed evident upfield shift from δ = to 5.53 ppm close to value of previously reported [(Ph 3 P) 2 Ag] 2 CO 3 (6.57 ppm). Figure S2. Attempted carboxylative cyclization of propargyl alcohol 1a with CO 2 catalyzed by silver complex isolated after reaction for 2 hours. Note: after the reaction, solid was precipitated and then collected for the next run after removing the product by diethyl ether. S4
6 Figure S3. Formation pathway for linear carbonates 3l and 3m. The reaction conditions: 1 (2.5 mmol), fresh prepared [(Ph 3 P) 2 Ag] 2 CO 3 (34 mg, 1 mol% relative to 1) under 1 bar CO 2 at 25 o C. GC yields were based on the propargylic alcohols. Effect of the catalyst amount on the carboxylic cyclization of propargylic alcohol 2a with CO 2. [a] [a] Reaction conditions: 1a (0.211 g, 2.5 mmol), Catalyst: [(Ph 3 P) 2 Ag] 2 CO 3, CHCl 3 (1.0 ml), CO 2 balloon, 25 o C, 1 h. NMR yield CO 2 Labeling Experiment Synthesis of 13 C carbonyl -labeled α-alkylidene cyclic carbonate (2a) by carboxylative cyclization of 2-methylbut-3-yn-2-ol with 13 CO 2. A 10-mL Schlenk tube equipped with a stirrer bar was charged with Ag 2 CO 3 (3.5 mg, 0.5 mol%), PPh 3 (13.1 mg, 2 mol%), propargylic alcohol (1a, 211 mg, 2.5 mmol) and CHCl 3 (0.5 ml). Next, the Schlenk tube was attached to a balloon filled with 13 CO 2 ( 13 C 99%). Then, the reaction mixture was stirred at 25 C for 2 h, and the mixture was extracted with Et 2 O (3 5 ml). The combined organic phase was concentrated in vacuo and purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the 13 C carbonyl -labeled α-alkylidene cyclic carbonate (2a) (296 mg, 92% yield). 1 H NMR (CDCl 3, 400 MHz) δ 4.75 (d, J = 4.0 Hz, 1H), 4.31 S5
7 (d, J = 4.0 Hz, 1H), 1.59 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ (C=O), 27.6 (-CH 3 ) ppm. IR (cm -1 ) (neat) 2990, 1788, HRMS (ESI, m/z) calcd. for C 5 13 CH 9 O 3 [M+H] + : , found: Figure S4. 13 C NMR spectrum of 13 C carbonyl -labeled α-alkylidene cyclic carbonate (2a) Figure S5. HRMS of 13 C carbonyl -labeled α-alkylidene cyclic carbonate (2a) S6
8 Silver-catalyzed three-component reaction of 2-methylbut-3-yn-2-ol, piperidine amines and 13 CO 2. The reactions were conducted in a 10-mL Schlenk tube equipped with a stirrer bar was charged with Ag 2 CO 3 (8.3 mg, 1.5 mol%), Ph 3 P (31.5 mg, 6 mol%), 2-methylbut-3-yn-2-ol (168.2mg, 2 mmol), secondary amines (170.2 mg, 2 mmol) and CH 3 CN (1 ml). Next, the Schlenk tube was attached to a balloon filled with 13 CO 2 ( 13 C 99%), and was sealed and heated at 30 C for 16 h. When the reaction completed, the vessel was cooled to room temperature. The residue was flushed with 3 5 ml CH 2 Cl 2 and removed under vacuum. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the 13 C carbonyl -labeled products (4a) (0.420 mg, 98% yield). 1 H NMR (CDCl 3, 400 MHz) δ 3.39 (m, 4H), 2.11 (s, 3H), (m, 6H), 1.43 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 154.2, (N-C=O) ppm. IR (cm -1 ) (neat), 2989, 2939, 2856, 1723, HRMS (ESI, m/z): C CH 20 NO 3 for [M+H] + calculated , found Figure S6. 13 C NMR spectrum of 13 C carbonyl -labeled β-oxopropylcarbamate (4a) S7
9 Figure S7. HRMS of 13 C carbonyl -labeled β-oxopropylcarbamate (4a) 3. DFT calculations DFT calculations were performed assisted by GAUSSIAN 09 program packages [3]. The calculation of stabilization energy (SE) in zero point energy (ZPE) form was carried out in order to assess the stability of these two models:. Relative activation energy (RAE) was carried out: RAE = E a - (E sub1 +E sub2 ). All the structures were optimized at B3LYP [4] /BSI level, where BSI signifies basis set LANL2DZ [5] performed for Ag atom and basis set 6-31G* [6] for other nonmetal main group atoms. Furthermore, all the structures were characterized and confirmed by frequency calculations to be energy minima. Solvent effect was also been taken into consideration when energy was involving by SMD [7] salvation model. Single point energy calculations were performed at M06 [8] / G** [6,9] /LANL2DZ//B3LYP/BSI level in toluene (ε = 2.374) solvent, where basis set G** was employed to C, H, O, N atoms while basis set LANL2DZ was employed to Ag atom. All energy data reported in this study were in kcal/mol, as well as the length data were in angstroms (Å). Structure visualizing program CYLview [10] were utilizing to generate relative figures. Molecular coordinates I-a C H H C H H S8
10 C H N C H H N C H H H C H C C C H H H C H H H O C O O H Ag C O C H H H O II-b P P Ag O H H S9
11 H C H H H H H H H C H H H C H H H C H H H C H C C C H H H C H H H O C O O P P Ag C H H H S10
12 C H H H C H H H C H H H C H H H C H H H Reference [1] H. Miyamoto, S. Yasaka, K. Tanaka, Bull. Chem. Soc. Jpn. 2001, 74, [2] G. A. Bowmaker, Effendy, J. V. Hanna, P. C. Healy, S. P. King, C. Pettinari, B. W. Skelton and A. H. White, Dalton Trans. 2011, 40, [3] M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, [4] a) C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, ; b) B. Miehlich, A. Savin, H.Stoll, H. Preuss Chem. Phys. Lett. 1989, 157, ; c) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch J. Phys. Chem. 1994, 98, [5] W. R. Wadt, P. J. Hay J. Chem. Phys. 1985, 82, [6] M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, [7] A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, [8] a) Y. Zhao, D. G.Truhlar, Acc. Chem. Res. 2008, 41, ; b) Y. Zhao, D. G. Truhlar, J. Chem. Theory Comput. 2009, 5, ; c) P. Sliwa, Handzlik, J. Chem. Phys. Lett. 2010, 493, ; d) A. D. Kulkarni, D. G. Truhlar, J. Chem. Theory Comput. 2011, 7, [9] a) A. J. H. Wachters, J. Chem. Phys. 1970, 52, ; b) P. J. Hay, J. Chem. Phys. 1977, 66, ; c) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, ; d) T. Clark, J. Chandrasekhar, G. W. Spitznagel, P. V. R. Schleyer, J. Comput. Chem. 1983, 4, ; e) M. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 80, ; f) K. Raghavachari, G. W. Trucks, J. Chem. Phys. 1989, 91, ; g) R. C. S11
13 Binning, L. A. Curtiss, J. Comput. Chem. 1990, 11, ; h) M. P. McGrath, L. Radom, J. Chem. Phys. 1991, 94, [10] C. Y. Legault, CYLview, 1.0b, niversit de Sherbroo e Sherbroo e ( u bec) Canada, 2009, 4. Characterization Data for Substrate and Products 1j Colourless solid. 1 H NMR (CDCl 3, 400 MHz) δ (m, 2H), (m, 3H), 2.09 (1H, OH), 1.62 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 131.6, 128.2, 122.7, 93.7, 82.1, 65.6, 31.5 ppm. 1k Straw yellow solid. 1 H NMR (CDCl 3, 400 MHz) δ (m, 5H), 2.15 (1H, OH), (m, 10H) ppm. 13 C NMR (CDCl 3, MHz) δ 131.6, 128.2, , 122.9, 92.8, 84.3, 69.1, 40.0, 25.2, 23.4 ppm. 2a Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (dd, J = 4.0 Hz, J = 4.0 Hz, 2H, CH 2 ), 1.59 (s, 6H, 2CH 3 ) ppm. 13 C NMR (CDCl 3, MHz) δ 158.6, (C=O), 85.2, 84.6, 27.5 ppm. MS (EI, 70 ev) m/z (%) = (2.81), (6.49), (100), (3.54), (48.16). IR (neat) 1825, 1687, 1271, 1086, 1032, 856 cm -1. 2b Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 4.80 (d, J = 4.0 Hz, 1H), 4.26 (d, J = 4.0 Hz, 1H), (m, 2H), 1.57 (s, 3H), 0.97 (t, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 157.2, 151.4, 87.5, 85.4, 33.1, 25.7, 7.1 ppm. GC-MS (EI, 70 ev) m/z (%) = (6), (16), (30), (75), (100). 2c Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 4.77 (d, J = 4.0 Hz, 1H), 4.26 (d, J = 4.0 Hz, 1H), (m, 2H), 1.57 (s, 3H), (m, 8H), 0.86 (t, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 157.7, 151.5, 87.2, 85.4, 40.4, 31.4, 28.9, 26.3, 22.8, 22.4, 13.9 ppm. GC-MS (EI, 70 ev) S12
14 m/z (%) = ([M+H] +, 2), (13), (35), (51), (68), (30), (45), (72), (29), (75), (93), (100). 2d Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (dd, 2H), (m, 3H), 1.57 (s, 3H), 0.96 (6H) ppm. 13 C NMR (CDCl 3, MHz) δ 158.1, 151.4, 87.3, 85.5, 48.3, 26.9, 24.2, 23.8, 23.5 ppm. GC-MS (EI, 70 ev) m/z (%) = (8), (8), (19), (37), (15), (10), (100). 2e Greenish-yellow oil. 1 H NMR (CDCl 3, 400 MHz) δ (m, 2H), (m, 3H), 4.95 (d, J = 4.0 Hz, 1H), 4.48 (d, J = 4.0 Hz, 1H), 1.97 (s, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 157.2, 151.0, 139.1, 129.0, 128.8, 124.5, 88.1, 87.0, 27.3 ppm. GC-MS (EI, 70 ev) m/z (%) = (13), (19), (100), (82), (52), (32), (43). 2f Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (m, 1H), (dd, 2H), (dd, 2H), 1.67 (s, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 156.0, 151.0, 136.0, 116.5, 87.2, 85.7, 25.5 ppm. GC-MS (EI, 70 ev) m/z (%) = (16), (50), (51), (39), (100). 2g Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 4.73 (d, J = 4.0 Hz, 1H), 4.28 (d, J = 4.0 Hz, 1H), (m, 2H), (m, 7H), (m, 1H) ppm. 13 C NMR (CDCl 3, MHz) δ 158.4, 151.2, 86.2, 85.3, 36.2, 24.0, 21.4 ppm. GC-MS (EI, 70 ev) m/z (%) = (9), (15), (15), (49), (50), (20), (100). 2h Straw yellow oil. 1 H NMR (CDCl 3, 400 MHz) δ 4.76 (d, J = 3.6 Hz, 1H), 4.33 (d, J = 4.0 Hz, 1 H), (m, 2H), (m, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 157.6, 151.4, 94.1, 85.3, 40.5, 24.1 ppm. GC-MS (EI, 70 ev) m/z (%) = ([M-44] +, 6), (15), (6), (77), (100), (24), (6). S13
15 2i Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 4.82 (d, J = 4.0 Hz, 1H), 4.27 (d, J = 4.0 Hz, 1 H), (m, 1H), 1.57 (s, 3H), (dd, J = 8.0 Hz, J = 8.0 Hz, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 157.1, 151.7, 89.8, 86.2, 36.9, 24.0, 16.3, 16.0 ppm. GC-MS (EI, 70 ev) m/z (%) = (6), (20), (100). 2j Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (m, 2H), (m, 2H), (m, 1H), 5.43 (s, 1H), 1.61 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 151.2, 150.7, 132.3, 128.6, 128.4, 127.5, 101.5, 85.5, 27.6 ppm. GC-MS (EI, 70 ev) m/z (%) = 204 (9), 160 (24), 145 (26), 132 (69), 117 (100), 115 (30), 91 (19), 89 (14). 2k White solid. 1 H NMR (CDCl 3, 400 MHz) δ (m, 5H), 5.47 (s, 1H), (m, 10H) ppm. 13 C NMR (CDCl 3, MHz) δ 151.4, 150.9, 132.5, 128.6, 128.4, 127.4, 101.7, 87.3, 36.6, 24.3, 21.7 ppm. GC-MS (EI, 70 ev) m/z (%) = (3), (2), (11), (10), (5), (8), (9), (100), (68), (20), (39), (15), (49), (8). 3l Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (1H), (1H), (1H), (3H), (3H), (3H) ppm. 13 C NMR (CDCl 3, MHz) δ 205.2, 204.8, 153.5, 81.0, 80.9, 78.3, 78.1, 74.1, 74.0, 64.5, 64.4, 25.5, 25.3, 21.1, 21.0, 16.1, 16.0 ppm. GC-MS (EI, 70 ev) m/z (%) = (6), (21), (13), (10), (18), (26), (100), (48). 3m Straw yellow oil. 1 H NMR (CDCl 3, 400 MHz) δ (m, 1H), (m, 1H), 2.51 (s, 1H), 2.15 (s, 3H), (m, 4H), (m, 4H), (m, 8H), (t, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 205.2, 204.7, 154.0, 82.1, 81.9, 80.24, 80.15, 74.7, 74.6, 68.4, 68.3, 34.4, 31.2, 31.1, 30.4, 25.8, 24.5, 24.4, 24.3, 22.34, 22.28, ppm. GC-MS (EI, 70 ev) m/z (%) = (6), (19), (7), 95 (12), (8), (8), (36), (28), (100), (23), (61). S14
16 4a Light brown oil. 1 H NMR (CDCl 3, 400 MHz) δ 3.39 (m, 4H, 2N-CH 2 ), 2.11 (s, 3H, COCH 3 ), (m, 6H, -CH 2 CH 2 CH 2 -), 1.43 (s, 6H, 2CH 3 ) ppm. 13 C NMR (CDCl 3, MHz) δ (C=O), (N-C=O), 82.7, 44.6, 25.6, 24.0, 23.4, 23.2 ppm. GC-MS (EI, 70 ev) m/z (%) = (0.33), (1.66), (15.03), (1.20), (12.49), (1.02), (8.01), (100), (45.97). IR (neat) 1827, 1685, 1271, 1172, 1085, 1031 cm -1. 4b Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 3.40 (4H), 2.09 (s, 3H), (m, 1H), (m, 1H), (2H), (4H), 1.42 (s, 1H) ppm. 13 C NMR (CDCl 3, MHz) δ (C=O), (N-C=O), 85.4, 44.8, 29.4, 25.7, 24.2, 24.0, 19.8, 7.6. MS (EI, 70 ev) m/z (%) (16.95), (100). 4c 1 H NMR (CDCl 3, 400 MHz) δ (m, 4H), 2.09 (s, 3H), (m, 12H), 0.92 (6H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.9, 154.1, 85.7, 45.2, 44.7, 44.4, 25.9, 24.5, 24.2, 23.6, 23.8, 23.7, 20.6 ppm. GC-MS (EI, 70 ev) m/z (%) (5.19), (100), (32.66). HRMS (ESI, m/z): C 14 H 26 NO 3 for [M+H] + calculated , found d 1 H NMR (CDCl 3, 400 MHz) δ 3.40 (m, 4H), 2.11 (s, 3H), (m, 1H), (m, 18H), 0.87 (s, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.8, 154.0, 85.2, 45.1, 44.7, 36.4, 31.5, 29.3, 25.7, 24.2, 23.9, 23.0, 22.4, 20.3, 13.9 ppm. GC-MS (EI, 70 ev) m/z (%) (6), (8), (100), (25). HRMS (ESI, m/z): C 16 H 30 NO 3 for [M+H] + calculated , found e 1 H NMR (CDCl 3, 400 MHz) δ (dd, J = 16 Hz, 1H), (dd, J = 16 Hz, J = 52 Hz, 2H), (m, 4H), 2.06 (s, 3H), (9 H) ppm. 13 C NMR (CDCl 3, MHz) δ 204.9, 153.7, 137.1, 115.5, 85.2, 45.2, 44.8, 25.9, 25.6, 24.1, 23.4, 21.7 ppm. GC-MS (EI, 70 ev) m/z (%) (100), (15), (45). HRMS (ESI, m/z): C 12 H 20 NO 3 for [M+H] + calculated , found f S15
17 Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ (4H), 2.06 (s, 3H), (2H), (m, 13H), (1H) ppm. 13 C NMR (CDCl 3, MHz) δ (C=O), (N-C=O), 84.1, 45.2, 44.6, 30.8, 25.9, 25.0, 24.2, 23.4, 21.4 ppm. MS (EI, 70 ev) m/z (%) = (12.33), (100), (27.49). HRMS (ESI, m/z): C 14 H 24 NO 3 for [M+H] + calculated , found g 1 H NMR (CDCl 3, 400 MHz) δ (5H), (m, 4H), 1.96 (s, 3H), 1.85 (s, 3H), (6H) ppm. 13 C NMR (CDCl 3, MHz) δ 204.2, 153.6, 139.5, 128.5, 127.8, 124.6, 86.8, 45.4, 44.9, 26.0, 25.5, 24.2, 23.5 ppm. GC-MS (EI, 70 ev) m/z (%) (19.09), (9.12), (7.89), (100), (21.07), (38.74). 4h 1 H NMR (CDCl 3, 400 MHz) δ (m, 1H), (m, 4H), 2.11 (s, 3H), (m, 6H), (J = 8 Hz, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.1, 154.4, 75.4, 44.9, 25.7, 25.4, 24.2, 16.1 ppm. GC-MS (EI, 70 ev) m/z (%) (12.86), (100), (18.35), (57.60). HRMS (ESI, m/z): C 10 H 18 NO 3 for [M+H] + calculated , found i 1 H NMR (CDCl 3, 400 MHz) δ (m, 1H), (m, 4H), 2.12 (s, 3H), (m, 14H), 0.86 (t, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.0, 154.7, 79.2, 45.0, 31.3, 30.4, 25.9, 25.8, 25.5, 24.9, 24.3, 22.3, 13.9 ppm. GC-MS (EI, 70 ev) m/z (%) (100), (30.39). HRMS (ESI, m/z): C 14 H 26 NO 3 for [M+H] + calculated , found j 1 H NMR (CDCl 3, 400 MHz) δ 4.84 (1H), (m, 4H), 2.10 (s, 3H), (m, 16H), 0.88 (t, 3H) ppm. 13 C NMR (CDCl 3, MHz) δ 206.9, 155.6, 79.1, 47.3, 46.8, 31.3, 30.7, 30.4, 30.1, 25.8, 24.8, 22.3, 19.9, 13.8, 13.7 ppm. GC-MS (EI, 70 ev) m/z (%) (8.59), (100), (25.18), (42.86). HRMS (ESI, m/z): C 17 H 34 NO 3 for [M+H] + calculated , found k Colourless oil. 1 H NMR (CDCl 3, 400 MHz) δ 3.37 (m, 4H), 2.14 (s, 3H), 1.87 (m, 4H), 1.45 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 208.0, 153.8, 62.8, 46.0, 23.8, 23.6 ppm. GC-MS (EI, 70 ev) m/z (%) = (1), (2), (19), (1), (8), (100). S16
18 4l Orange solid. M.p o C 1 H NMR (CDCl 3, 400 MHz) δ 3.62 (t, J = 4.0 Hz, 4H), 3.43 (t, J = 20.0 Hz, 4H), 2.09 (s, 3H), 1.42 (s, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.2, 154.0, 83.3, 66.5, 44.5, 43.6, 23.5, 23.5 ppm. GC-MS (EI, 70 ev) m/z (%) = (1.46), (1.96), (18.30), (6.22), (100), (2.10), (48.56), (1.69). 4m Straw yellow oil. 1 H NMR (CDCl 3, 400 MHz) δ (q, 4H, CH 2 ), 2.12 (s, 3H), 1.45 (s, 6H), 1.14 (m, 6H) ppm. 13 C NMR (CDCl 3, MHz) δ 207.7, 154.6, 82.8, 41.8, 41.6, 23.6, 23.4, 14.1, 13.5 ppm. GC-MS (EI, 70 ev) m/z (%) = (0.26), (1.72), (16.15), (3.34), (6.35), (100), (46.64). 4n Yellow oil. 1 H NMR (CDCl 3, 400 MHz) δ 3.20 (t, 4H), 2.11 (s, 3H), (m, 4H), 1.43 (s, 6H), (m, 4H), 0.92 (6H) ppm. 13 C NMR (CDCl 3, MHz) δ (C=O), (N-C=O), 82.8, 47.0, 46.7, 30.8, 30.1, 23.6, 23.3, 19.9, 13.8 ppm. GC-MS (EI, 70 ev) m/z (%) = (1), (2), (12), (1), (12), (10), (100), (2), (35), (7), (2), (27), (14). S17
19 5. NMR Spectral Copies of the Substrates and Products 1j 1 H NMR (CDCl 3, 400 MHz) 1j 13 C NMR (CDCl 3, MHz) S18
20 1k 1 H NMR (CDCl 3, 400 MHz) 1k 13 C NMR (CDCl 3, MHz) S19
21 2a 1 H NMR (CDCl 3, 400 MHz) 2a 13 C NMR (CDCl 3, MHz) S20
22 2b 1 H NMR (CDCl 3, 400 MHz) 2b 13 C NMR (CDCl 3, MHz) S21
23 2c 1 H NMR (CDCl 3, 400 MHz) 2c 13 C NMR (CDCl 3, MHz) S22
24 2d 1 H NMR (CDCl 3, 400 MHz) 2d 13 C NMR (CDCl 3, MHz) S23
25 2e 1 H NMR (CDCl 3, 400 MHz) 2e 13 C NMR (CDCl 3, MHz) S24
26 2f 1 H NMR (CDCl 3, 400 MHz) 2f 13 C NMR (CDCl 3, MHz) S25
27 2g 1 H NMR (CDCl 3, 400 MHz) 2g 13 C NMR (CDCl 3, MHz) S26
28 2h 1 H NMR (CDCl 3, 400 MHz) 2h 13 C NMR (CDCl 3, MHz) S27
29 2i 1 H NMR (CDCl 3, 400 MHz) 2i 13 C NMR (CDCl 3, MHz) S28
30 2j 1 H NMR (CDCl 3, 400 MHz) 2j 13 C NMR (CDCl 3, MHz) S29
31 2k 1 H NMR (CDCl 3, 400 MHz) 2k 13 C NMR (CDCl 3, MHz) S30
32 3l 1 H NMR (CDCl 3, 400 MHz) 3l 13 C NMR (CDCl 3, MHz) S31
33 3m 1 H NMR (CDCl 3, 400 MHz) 3m 13 C NMR (CDCl 3, MHz) S32
34 4a 1 H NMR (CDCl 3, 400 MHz) 4a 13 C NMR (CDCl 3, MHz) S33
35 4b 1 H NMR (CDCl 3, 400 MHz) 4b 13 C NMR (CDCl 3, MHz) S34
36 4c 1 H NMR (CDCl 3, 400 MHz) 4c 13 C NMR (CDCl 3, MHz) S35
37 4d 1 H NMR (CDCl 3, 400 MHz) 4d 13 C NMR (CDCl 3, MHz) S36
38 4e 1 H NMR (CDCl 3, 400 MHz) 4e 13 C NMR (CDCl 3, MHz) S37
39 4f 1 H NMR (CDCl 3, 400 MHz) 4f 13 C NMR (CDCl 3, MHz) S38
40 4g 1 H NMR (CDCl 3, 400 MHz) 4g 13 C NMR (CDCl 3, MHz) S39
41 4h 1 H NMR (CDCl 3, 400 MHz) 4h 13 C NMR (CDCl 3, MHz) S40
42 4i 1 H NMR (CDCl 3, 400 MHz) 4i 13 C NMR (CDCl 3, MHz) S41
43 4j 1 H NMR (CDCl 3, 400 MHz) 4j 13 C NMR (CDCl 3, MHz) S42
44 4k 1 H NMR (CDCl 3, 400 MHz) 4k 13 C NMR (CDCl 3, MHz) S43
45 4l 1 H NMR (CDCl 3, 400 MHz) 4l 13 C NMR (CDCl 3, MHz) S44
46 4m 1 H NMR (CDCl 3, 400 MHz) 4m 13 C NMR (CDCl 3, MHz) S45
47 4n 1 H NMR (CDCl 3, 400 MHz) 4n 13 C NMR (CDCl 3, MHz) S46
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