Homologation of Boronic Esters using OrganoLithium
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1 Homologation of Boronic Esters using OrganoLithium Varinder Kumar Aggarwal* Angew. Chem. Int. Ed., 2014, 54, Acc. Chem. Res., 2014, 47, Chem. Eur. J., 2011, 17, Report: Zhe Dong Advisor: Prof. Guangbin Dong March 28 th
2 Varinder Kumar Aggarwal BS in chemistry, Cambridge University 1983 PHD : Prof. Stuart Warren Cambridge University Prof. Gilbert Stork, Columbia University Lecturer in Chemistry, Bath University, Lecturer in Chemistry, Sheffield University ( ) Reader in Chemistry, Sheffield University ( ) Professor in Chemistry, Sheffield University (Oct Sept. 2000). Professor in Synthetic Chemistry, Bristol University (Sept present). 2
3 First Homologation of Boronic Esters Matteson, D. S.; Ray, R. J. Am. Chem. Soc. 1980, 102, 7590 Carbene Insertion Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. Nat. Chem. 2009, 1, 494 Peng, C.; Zhang, W.; Yan, G.; Wang, J. Org. Lett. 2009, 11,
4 From Carbene To yilde V. K Aggarwal, G. Yu Fang, A. Schmidt, J. Am. Chem. Soc., 2005, 127,
5 Mechanism Containing 1,2-metallate Migration V. K Aggarwal, G. Yu Fang, A. Schmidt, J. Am. Chem. Soc., 2005, 127,
6 Selectivity of Asymmetric Borate for 1,2-metallate Migration R. Robiette, G. Y. Fang, J. N. Harvey, V. K. Aggarwal, Chem. Commun., 2006,
7 2+1 reaction : From vinyl Nuc to allyl Nuc G. Y. Fang, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
8 1,3 Asymmetric Crotylation G. Y. Fang, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
9 1,1 Asymmetric Crotylation G. Y. Fang, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
10 Diastereoselectivity Model Asymmetric Crotylation G. Y. Fang, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
11 Selectivity of 9-BBN Borate for 1,2-metallate Migration G. Y. Fang, O. A. Wallner, N. Di Blasio, X Ginesta, J. N. Harvey, V, K. Aggarwal, J. Am. Chem. Soc., 2007, 129,
12 From Sulfur Yilde to Chiral Lithium Carbamate J. L. Stymiest, G. Dutheuil, A. Mahmood, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
13 Stereodivergent Synthesis: J. L. Stymiest, G. Dutheuil, A. Mahmood, V. K. Aggarwal, Angew. Chem. Int. Ed., 2007, 46,
14 From Chiral Carbamate to Chiral Boronate J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal,Nature, 2008, 456,
15 Explanation for Retention and Inversion J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature, 2008, 456,
16 Chiral Lithium Generated From Chiral Epoxide E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal,Org. Lett. 2009, 11,
17 Chiral Lithium Generated From Chiral Azaridine F. Schmidt, F. Keller, E. Vedrenne, V. K. Aggarwal, Angew. Chem. Int. Ed., 2009, 48,
18 F. Schmidt, F. Keller, E. Vedrenne, V. K. Aggarwal, Angew. Chem. Int. Ed., 2009, 48,
19 Rh(I) catalyzed Stereospecific Transfer to Form Quaternary Carbon A. Ros, V. K. Aggarwal,Angew. Chem. Int. Ed., 2009, 48,
20 Total Synthesis of (+)-Faranal* G. Dutheuil, M. P. Webster, P. A. Worthington, V. K. Aggarwal,Angew. Chem. Int. Ed., 2009, 48,
21 Stereodivergent Crotylation M. Althaus, A. Mahmood, J. Ramón Suárez, S. P. Thomas, V. K. Aggarwal,J. Am.Chem.Soc., 2010, 132,
22 Class I Crotylation M. Althaus, A. Mahmood, J. Ramón Suárez, S. P. Thomas, V. K. Aggarwal,J. Am.Chem.Soc., 2010, 132,
23 Class II Crotylation M. Althaus, A. Mahmood, J. Ramón Suárez, S. P. Thomas, V. K. Aggarwal,J. Am.Chem.Soc., 2010, 132,
24 Class III Crotylation M. Althaus, A. Mahmood, J. Ramón Suárez, S. P. Thomas, V. K. Aggarwal,J. Am.Chem.Soc., 2010, 132,
25 Unusual Inversion during 1,2 metallate migration M. Binanzer, G. Y. Fang, V. K. Aggarwal,Angew. Chem. Int. Ed., 2010, 49,
26 Unusual Inversion during 1,2 metallate migration M. Binanzer, G. Y. Fang, V. K. Aggarwal,Angew. Chem. Int. Ed., 2010, 49,
27 Total Synthesis of Solandelactone E: V. Bagutski, R. M. French, V. K. Aggarwal,Angew. Chem. Int. Ed., 2010, 49,
28 Improved 100% Charity Transfer V. Bagutski, R. M. French, V. K. Aggarwal,Angew. Chem. Int. Ed., 2010, 49,
29 Stereospecific Proto-deboranlation S. Nave, R. P. Sonawane, T. G. Elford, V. K. Aggarwal.J. Am. Chem. Soc., 2010, 132,
30 Stereospecific Proto-deboranlation S. Nave, R. P. Sonawane, T. G. Elford, V. K. Aggarwal.J. Am. Chem. Soc., 2010, 132,
31 Chiral Amine From Chiral Boron V. Bagutski, T. G. Elford, V. K. Aggarwal.Angew. Chem. Int. Ed., 2011, 50,
32 Using Zweifel Olefination To work up V. K. Aggarwal, M. Binanzer, M. Carolina de Ceglie, M. Gallanti, B. W. Glasspoole, S. J. F. Kendrick, R. P. Sonawane, A. Vazquez-Romero, M. P. Webster. Org. Lett., 2011, 13,
33 In-situ Cascade to form Quaternary Carbon R. P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H. K. Scott, V. K. Aggarwal, Angew. Chem. Int. Ed., 2011, 50,
34 In-situ Cascade to form Quaternary Carbon R. P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H. K. Scott, V. K. Aggarwal, Angew. Chem. Int. Ed., 2011, 50,
35 R. P. Sonawane, V. Jheengut, C. Rabalakos, R. Larouche-Gauthier, H. K. Scott, V. K. Aggarwal, Angew. Chem. Int. Ed., 2011, 50,
36 Total Synthesis of (+)-Erogorgiaene T. G. Elford, S. Nave, R. P. Sonawane, V. K. Aggarwal,J. Am. Chem. Soc., 2011, 133,
37 Total Synthesis of (+)-Erogorgiaene T. G. Elford, S. Nave, R. P. Sonawane, V. K. Aggarwal,J. Am. Chem. Soc., 2011, 133,
38 Chiral Organometallic Type Nucleophiles for Asymmetric Synthesis. A type orbital for SE2 Inservsion R. Larouche-Gauthier, T. G. Elford, V. K. Aggarwal,J. Am. Chem. Soc., 2011, 133,
39 Activating group Effect. Scope of electrophile R. Larouche-Gauthier, T. G. Elford, V. K. Aggarwal,J. Am. Chem. Soc., 2011, 133,
40 R. Larouche-Gauthier, T. G. Elford, V. K. Aggarwal,J. Am. Chem. Soc., 2011, 133,
41 OrganoLithium From Chiral Secondary Allylic Carbamates A. P. Pulis, V. K. Aggarwal,J. Am. Chem. Soc., 2012, 134,
42 Total Synthesis of C30 Botryococcene. A. P. Pulis, V. K. Aggarwal,J. Am. Chem. Soc., 2012, 134,
43 OrganoLithium From Chiral Secondary Propargyl Carbamates B. M. Partridge, L. Chausset-Boissarie, M. Burns, A. P. Pulis, V. K. Aggarwal, Angew. Chem. Int. Ed., 2012, 51,
44 From Propargyl Borate To chiral allene B. M. Partridge, L. Chausset-Boissarie, M. Burns, A. P. Pulis, V. K. Aggarwal, Angew. Chem. Int. Ed., 2012, 51,
45 Fine tuning Of α and γ Seletivite Protonation Of Ally boron M. J. Hesse, C. P. Butts, C. L. Willis, V. K. Aggarwal,Angew. Chem. Int. Ed., 2012, 51,
46 D.R. Model M. J. Hesse, C. P. Butts, C. L. Willis, V. K. Aggarwal,Angew. Chem. Int. Ed., 2012, 51,
47 A new protocol For Roush-type Aldehyde Allylation Jack L.-Y. Chen, Helen K Scott, Matthew J Hesse, Christine L. Willis, Varinder K. Aggarwal.J. Am. Chem. Soc., 2013, 135,
48 Method A, directly mix together, Method B, nbuli and TFAA activation Jack L.-Y. Chen, Helen K Scott, Matthew J Hesse, Christine L. Willis, Varinder K. Aggarwal.J. Am. Chem. Soc., 2013, 135,
49 A new protocol For Ketone Allylation Seterodivergent Synthesis Jack L.-Y. Chen, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
50 Ketone Allylation Jack L.-Y. Chen, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
51 Generate the Chiral Lithium at Unactivated Position Alexander P. Pulis, Daniel J. Blair, Eva Torres, and Varinder K. Aggarwal.JACS, 2013, 135,
52 14 used to Need 15 steps Alexander P. Pulis, Daniel J. Blair, Eva Torres, and Varinder K. Aggarwal.JACS, 2013, 135,
53 Transfer OH to Bpin Stefan Roesner, Christopher A. Brown, Maziar M. Mohiti, Alexander P. Pulis, Ramesh Rasappan, Daniel J. Blair, Stefanie Essafi, Daniele Leonori and Varinder K Aggarwal. Chem.Commun., 2014, 50,
54 Quaternary Carbon Center formation Daniel J. Blair, Catherine J. Fletcher, Katherine M. P. Wheelhouse, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
55 Daniel J. Blair, Catherine J. Fletcher, Katherine M. P. Wheelhouse, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
56 Daniel J. Blair, Catherine J. Fletcher, Katherine M. P. Wheelhouse, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
57 1,1 di-substituted allyl Bpin in the crotylation Matthew J. Hesse, Stéphanie Essafi, Charlotte G. Watson, Jeremy N. Harvey, David Hirst, Christine L. Willis, Varinder Aggarwal. Angew. Chem. Int. Ed., 2014, 53,
58 Quaternary Carbon Center formation Amadeu Bonet, Marcin Odachowski, Daniele Leonori, Stephanie Essafi, Varinder Aggarwal. Nat. Chem., 2014, 6,
59 Quaternary Carbon Center formation Amadeu Bonet, Marcin Odachowski, Daniele Leonori, Stephanie Essafi, Varinder Aggarwal. Nat. Chem., 2014, 6,
60 Mechanism for Quaternary Carbon Center formation Amadeu Bonet, Marcin Odachowski, Daniele Leonori, Stephanie Essafi, Varinder Aggarwal. Nat. Chem., 2014, 6,
61 Remove the unactivate Bpin Ramesh Rasappan, Varinder Aggarwal. Nat. Chem., 2014, 6,
62 Ramesh Rasappan, Varinder Aggarwal. Nat. Chem., 2014, 6,
63 Auto-synthesis Matthew Burns, Stéphanie Essafi, Jessica R. Bame, Stephanie P. Bull, Matthew P. Webster, Sébastien Balieu, James W. Dale, Craig P. Butts, Jeremy N. Harvey, Varinder K. Aggarwal. Nature, 2014, 513,
64 Only three example in the paper Matthew Burns, Stéphanie Essafi, Jessica R. Bame, Stephanie P. Bull, Matthew P. Webster, Sébastien Balieu, James W. Dale, Craig P. Butts, Jeremy N. Harvey, Varinder K. Aggarwal. Nature, 2014, 513,
65 Vicinal Quaternary Carbon Center formation Charlotte G. Watson, Angelica Balanta, Tim G. Elford, Stéphanie Essafi, Jeremy N. Harvey, Varinder K. Aggarwal.J. Am. Chem. Soc., 2014, 136,
66 Charlotte G. Watson, Angelica Balanta, Tim G. Elford, Stéphanie Essafi, Jeremy N. Harvey, Varinder K. Aggarwal.J. Am. Chem. Soc., 2014, 136,
67 C2/C4- alkylation of pyridine Josep Llaveria, Daniele Leonori, Varinder K. Aggarwal.J. Am. Chem. Soc., 2015, 137,
68 Josep Llaveria, Daniele Leonori, Varinder K. Aggarwal.J. Am. Chem. Soc., 2015, 137,
69 Chiral fluorine compound synthesis Christopher Sandford, Ramesh Rasappan, Varinder K. Aggarwal. J. Am. Chem. Soc., 2015, 137,
70 Christopher Sandford, Ramesh Rasappan, Varinder K. Aggarwal. J. Am. Chem. Soc., 2015, 137,
71 Pd-catalyzed Formal Three carbon Logation of Boronic Esters Phillip J. Unsworth, Dr. Daniele Leonori, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
72 Phillip J. Unsworth, Dr. Daniele Leonori, Varinder K. Aggarwal.Angew. Chem. Int. Ed., 2014, 53,
73 Merging the Metal catalysis And 1,2-metallate Migration. Zhang, G. J. Lovinger, E. K. Edelstein, A. A. Szymaniak, M. P. Chierchia and J. P. Morken, Science, 2016, 351, 70.
74 . Zhang, G. J. Lovinger, E. K. Edelstein, A. A. Szymaniak, M. P. Chierchia and J. P. Morken, Science, 2016, 351, 70.
75 Thank you for your attention
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