The Anomeric Effect. one gauche interaction. OMe. !!G o anomeric effect (stabilization) = "!G o (heterocycle) - "!G o (steric)

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1 Wednesdy, Nvember 9, 2005 Brn Grup eting Further eding: G..J. Thtcher (ed.), nd elted terelectrnic Effects. AC ympsium eries #539, eview: Juristi, E., Cuevs, G., Tetrhedrn, 1992, 48(24), istricl Aspects f the Anmeric Effect First bserved in 1955 by J.T. Edwrd nd in 1958 by.u. Lemieux. Anmeric Effect Defined (IUPAC): riginlly defined s the thermdynmic preference fr plr grups bnded t C-1 (the nmeric crbn f glycpyrnsyl derivtive) t tke up n xil psitin. Bth were studying crbhydrte chemistry nd nticed preference fr lkxy nd cetyl grups t reside in the xil psitin. Edwrd prpsed tht the lne pirs n the ring xygen were cntributing t the effect. ~1.5 kcl lkyl substituted cyclhexnes prefer equitril rienttin ver xil lkyl substituted tetrhydrpyrns shw this sme preference the nmeric crbn f the mst bundnt nturl sugr, D-glucpyrnse, ls prefers n equtril rienttin. 36% : 64% cnversin int methyl ether t the nmeric crbn prduces different result frm the bve substitutin with mre electrnegtive grups chnges the bserved rti t greter extent Ac Ac Ac Ac Ac Ac rti f preference gives us sme insight tht smething is different 67% : 33% different frm reigning cyclhexne cnfrmtinl nlysis mdel Ac Ac Ac 86% : 14% 94% : 6% Ac Ac Ac Ac Ac Ac Ac Ac Ac This effect is nw cnsidered t be specil cse f generl preference (the generlized nmeric effect) fr guche cnfrmtins but the bnd C Y in the system C Y C where nd Y re hetertms hving nnbnding electrn pirs, cmmnly t lest ne f which is nitrgen, xygen, sulfur r flurine. ne guche interctin - hs n xil preferecne in C1 substituted tetrhydrpyrn Y tw guche interctins Y preferred by generlized nmeric effect Electrnegtivites f elvnt Atms C N I 2.5 Br F 4.0!!G nmeric effect (stbiliztin) = "!G (hetercycle) - "!G (steric) Frnck,.W., Tetrhedrn, 1983, 39, electrnic fctr steric fctr Fr the nmeric stbiliztin t effect the cnfrmtin t ll it must be mre stblizing then the sum f ll f the steric fctrs Liner Exmple: ften referred t s the guche effect

2 Brn Grup eting vent ls plys rle: Increse in nmeric stbiliztin sscited with lw slvent diple lvent C 4 benzene C 3 cetne CN 2 Diple % xil Further Evidence: 1.43 Å e e 1.39 Å bnd lenght: incresed in the xil C- bnd (1.819Å) versus the equtril C- bnd (1.7181Å) mers, C., et l. Tpics terechem., 1969, 4, 39. xil bnd ls bserved t be lnger then equitril bnd in this cnstrined cse Lemieux,.U., et l. Cn. J. Chem. 1969, 47, Mst widely ccepted explntin fr the nmeric effect: hypercnjugtin resnce frm stblizes xil cnfrmtin 2 1 ser Exmintin f rbitls: bserved bnd length fr bnd 2 is shrter then typicl -C bnd nd lnger fr bnd 1 ther Explntins: Diple tbiliztin: ppsing diples re stblizing reltive t ligned diples destblizing diple interctin Electrsttic epulsin: Decresed electrsttic interctins re fvred M: nn-bnding (n xygen ) LUM: nti-bnding (!* C- ) stblizing 2 electrn interctin ntiperiplnr representtin This mdel is referd t s Antiperiplnr Lne Pir ypthesis r ALP destblizing interctin f electrnegtive tm guche with tw lne pirs destblizing interctin f electrnegtive tm guche with nly ne lne pir fvred Net Anmeric Effect prbbly due t cmbintin f fctrs

3 Brn Grup eting The Ex-Anmeric Effect: Effect is bserved in tetrhydrthipyrn: C 3 view here minr cntributin t verll resnnce reltive t end nmeric effect sme rbitl verlp with excyclic xygen bserved s stblizing resnnce frm Less significnt cntributin f nmeric effect with tetrhydrthipyrn. wever, since C- bnds re lnger then C-C bnds 1,3-dixil interctins re decresed nd s result mre xil ismer is seen then in the xygen nlgs Effect is bserved in dixnes nd dithines: ls cn be stblizing with equitril substituents Anmeric Effect f dicls: Ac Ac Ac Ac Ac Ac C 3 Ac Ac view here end nmeric effect is the dminnt stblizing interctin with xil substituents, the ex nmeric effect is strnger with equitril subsitutents Anmeric Effect=(ex-AE eq )-(ex-ae x +end-ae x ) end nmeric effect is bsent in the equitril cnfrm s this term is zer Prly, J. P., Lemieux,.U., Cn. J. Chem. 1987, 65, 213. Bu 3 n -20 C Bu 3 n -20 C Ac Ac Ac Ac Ac Ac Ac Ac Bu 3 nd Giese, B., Dupuis, J., Tetrhedrn Lett., 1983, 25, Ac Ac Ac Ac D Mjr Prduct 98:2 simple extentin f the tetrhydrpyrn cse hwever nw there re tw xygens tht tke prt in the resnnce structure dithines shw n even greter preference fr xil substituents due t greter relxtin f 1,3-dixil interctins Effect is very miniml with mine nitrgens: N 2 mine nitrgen nt electrnegtive enugh t prduce significnt nmeric effect n tetrhydrpyrn tructures with N-C- bnds where is strngly elcetrnegtive substitutent n piperdine re nt stble s the effect cnnt be studied n these systems Effects t sp 2 centers: incresed brrier f rttin due t stblizing interctin

4 Brn Grup eting pirketls: fund in mny nturl prducts structurl cnfrmtins tht depend n the nmeric effect reviews: Perrn, F., Albizti, K.F. Chem.ev. 1989, 89, Brimble, M.A., Furkert, D.P. Current rgnic Chemistry, 2003, 7, ct. cid 1 nmeric effect sterechemistry? Anmeric Cntrl f Prduct Distributin: kinetic pthwy PTA (ct.) thermdynmic pthwy 2 nmeric effects (mst stble) n nmeric effects (lest stble) high energy twist-bt cnfrmtin required fr Bürgi-Dunitz ngle 1 nmeric effect Generl cnsidertins fr spirketl ring systems. Actul utcme will ls be dependent n substituents kinetic cnditins 100:0 thermdynmic cnditins 45:55 e e G..J. Thtcher (ed.), nd elted terelectrnic Effects. AC ympsium eries #539, The everse Anmeric Effect: Fct r Fictin? Preference fr equtril psitin with psitively chrged-electrnegtive substituents C. L. Perrin, Tetrhedrn, 1995, 51, N 3 N 3 N 3 N 3 highly debted in the literture -ften the chrged species studied re bulky nd sterics hve greter cntributiin -diple interctins in equitril stte re nt stblizing (evidence fr this mdel) -n lne pir n xil subsituent t cntribute t the ex-nmeric effect -the xil structure is wek (fvred by elimintin) nd unlikely t exist, nly the equitril ismer is preferred s result interesting exceptin: N N tcliffe, A.J. Frser-eid, B. J.Chem. c. Perkin Trns ,

5 Brn Grup eting Brief mpling f imple pirketl Nturl Prducts: Nn-Anmeric spirketl: Frm: Perrn, F., Albizti, K.F. Chem.ev. 1989, 89, Agric. Bil. Chem., , rg. Lett., 2004, 6(21),

6 Brn Grup eting Et Ph w cn we use the nmeric effect? (+)-Lepicidin A: Bn Bn Bn TM TIP Ac Ph TM TEA Ph Ph Dnishefsky,. Lnger, M. J. rg. Chem. 1985, 50, Bn pure " nd! nmers used Et +, ct. Ph 3 C 4 87% F, C 3 CN NB CN = Bn Bn Bn Bn N tcliffe, A.J. Frser-eid, B. J.Chem. c. Perkin Trns ":! 17:1 cntrlled by nmeric effect =TIP Br Ag-Zelite C % Et NFmc Evns, D. A.; Blck W. C. J. Am. Chem. c. 1993,115, nmeric cntrl f xil! desired ismer 68% frm! nmer 64% frm " nmer N =Ac = NFmc ":! 6:1 nmeric effect gives undesired prduct = Disccchride frm Apptlidin: TETf =TE Ph TB " <! TB F 3 N(Et) 2 TB Bn Ph Ph 100% Ph n 2 Ph F Bn TB Ph wheres: TB Ph TE Bn bulky Ph grups used t discurge nmeric cntrl f prduct -Ni 92% TE F TB ":! 15:1 TE F 3 N(Et) 2 100% used in glycsyltin Niclu, K.C. et. l. J. Am. Chem. c. 2001, 125, % Pd 2 C, Cu 25 C, 25hrs 5% Pd 2 C, Cu 25 C, 25hrs 5% Pd 2 C, Cu 25 C, 25hrs 1:1 nly " ismer C C C >95 " ismer emmelhck, M.F., et l. Pure & Appl. Chem., 1990, 62(10), Pd Pd

7 Brn Grup eting ynthesis f pirtekls: equence 1: TP TP t-buli g, BF 3 Et 2 Br Br C % 40% Azspircid: bth frms shw nmeric stbliztin equence 2: LDA C I(C 2 ) 4 TB cmmn intermedite 3 PPh 3 34% Phtchemicl Cycliztin: "trns" TP 2 nmeric effects mjr prduct LiI, 2,6-lutidene C " 35% tw steps "cis" PPT 58% 4 nmeric effects strngly disfvred due t diple repulsin 1) Li(C 2 ) 4 TB, 74% 2) P3, py 64% 1.85:1 t 3.35:1 depending n slvent McGrvey, G.J., tepnin, M.W. Tet. Lett., 1996, 37(31), h! pta Nrrish type II Cttier, L.; Desctes, G. Tetrhedrn 1985, 41(2), ,5 hydrgen bstrctin h! " ct. Acid ismerize t nmericlly stblized ismer incrrect structure riginlly trgeted nd synthesized key spirketl step: TBDP TBDP TE * TE 4 disteremers 1 : 1 : 1 : 1 3: 1 : 0.9 : 0 * TMTf -90 C TBDP 89% Idine(III) medited rdicl cycliztin t pircetls: PhI(Ac) 2 I 2, h! 90% pta, C 2 2 TBDP F, py spirlides B nd D Brimble, M. A. Mlecules. 2004, 9, crrect structure s cmpred t nturl prduct Niclu, K.C., et l. Angew. Chem. Int. Ed. 2004, 43, =TE = TBDP PhI(Ac) 2 I 2, h!

8 Brn Grup eting Exmples f pirketl Tethering: Pusn-Khnd lefin tthesis Bn TBDP Tf 2 N 89 % Bn 100%! TBDP Grubbs Gen-1 10 ml % 95% Bn TBDP will be pplied t the synthesis f spirstrelllide A Ac Ac C 2 (C) 8 3 N 91% C 2 (C) 8 3 N 90% Ac Ac [cis:trns] [95:< 5] side rectin underges slw elimintin side rectin underges fcile elimintin Diels Alder Bn Bn TB Liu, J., sung,. P., rg. Lett. 2005, 7(11), PPT C % TB TB Bn Bn TB 1) TBAF 2) TBCL, imidzle 3) TPAP, NM 66% three steps E xil A nti [cis:trns] [< 5:95] prbble trnsitin stte tw nmeric effects nd tw chir cnfrmtins 5 membered ring: Ac C 2 (C) 8 3 N 78% Ac TB Bn 1) LMD TB Bn TB nmeric cntrl dmintes sterechemicl utcme even if substituent is frced int xil psitin Bn 2) N I K 2 C 3 Zn 2 Bn C C-.T. Bn Bn Ac C 2 (C) 8 3 N = 63% =Et 50% Ac Ac C 2 (C) 8 3 N = 49% =Et 40% Ac fvred trnsitin stte leding t prduct xil LA xil end-bt-bt w/ tw nmeric effects nly disteremer P finlly ble t frce selectivity with bulky silyl grup - sterics bet nmeric effect C 2 (C) 8 3 N 100 P C 40% P=TE [cis:trns] [36:64] P=TB [cis:trns] [10:90] P=TBDP [cis:trns] [< 5:95] equitril P Wng, J., sung,. P., Ghsh,.K. rg. Lett. 2005, 6(12), Ghsh,.K., sung,.p., Liu, J. J. Am. Chem. c. 2005, 127,

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