Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates

Science China Chemistry

Volumn 54, Issue 1, 2011, Pages 81-86

  Peng, Jing ^a   Cui, Hailei ^a   Chen, Yingchun ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

asymmetric allylic alkylation; cinchona alkaloids; Morita Baylis Hillman carbonates; organocatalysis; sulfonylimidates

Indexed keywords

ASYMMETRIC ALLYLIC ALKYLATIONS; CINCHONA ALKALOID; MORITA-BAYLIS-HILLMAN CARBONATES; ORGANOCATALYSIS; SULFONYLIMIDATES;

ALKYLATION; CARBONATES; CATALYSIS; METABOLITES; NITROGEN COMPOUNDS; REACTION KINETICS;

RATE CONSTANTS;

EID: 79251572964     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4137-2     Document Type: Conference Paper

References (28)

1. E.J. Yoo I. Bae S.H. Cho H. Han S. Chang 2006 A facile access to N-sulfonylimidates and their synthetic utility for the transformation to amidines and amides Org Lett 8 1347 1350 1:CAS:528:DC%2BD28XitVOjtLg%3D 10.1021/ol060056j
2. J.D. Larsen H. Bundgaard 1989 Prodrug forms for the sulfonamide group III chemical and enzymatic hydrolysis of various N-sulfonyl imidates-a novel prodrug form for a sulfonamide group or an ester function Int J Pharm 51 27 38 1:CAS:528:DyaL1MXktFagu7Y%3D 10.1016/0378-5173(89)90071-9
3. R. Kupfer M. Nagel E.U. Würthwein R. Allrnann 1985 Synthese und struktur von N-acylimidsaureestern Chem Ber 118 3089 3104 1:CAS:528: DyaL2MXlvFGrsrc%3D 10.1002/cber.19851180808
4. R. Matsubara F. Berthiol S. Kobayashi 2008 Sulfonylimidates as nucleophiles in catalytic addition reactions J Am Chem Soc 130 1804 1805 1:CAS:528:DC%2BD1cXmtlamuw%3D%3D 10.1021/ja077054u
5. R. Matsubara S. Kobayashi 2008 DBU-catalyzed addition reactions of sulfonylimidates Synthesis 18 3009 3011
6. Kan SBJ, Matsubara R, Berthio F, Kobayashi S. Catalytic direct-type substitution reaction of α-alkyl enolates: A Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates. Chem Commun, 2008, 6354-6356
7. H.V. Nguyen R. Matsubara S. Kobayashi 2009 Addition reactions of sulfonylimidates with imines catalyzed by alkaline earth metals Angew Chem Int Ed 48 5927 5929 10.1002/anie.200900309
8. A. Massa N. Utsumi C.F. Barbas III 2009 N-tosylimidates in highly enantioselective organocatalytic michael reactions Tetrahedron Lett. 50 145 147 1:CAS:528:DC%2BD1cXhsVOms7vL 10.1016/j.tetlet.2008.10.126
9. R. Matsubara F. Berthiol H.V. Nguyen S. Kobayashi 2009 Catalytic mannich-type reactions of sulfonylimidates Bull Chem Soc Jpn 82 1083 1102 1:CAS:528:DC%2BD1MXht1erurvE 10.1246/bcsj.82.1083
10. R. Matsubara S. Kobayashi 2009 Catalytic carbanion reactions: formation and reaction of carbanions from ester or amide equivalents using catalytic amounts of bases Chem Eur J 15 10694 10700 10.1002/chem.200901515
11. B.M. Trost F.D. Toste 1998 Asymmetric O- and C-alkylation of phenols J Am Chem Soc 120 815 816 1:CAS:528:DyaK1cXmvFWgsw%3D%3D 10.1021/ja972453i
12. B.M. Trost H.C. Tsui F.D. Toste 2000 Deracemization of Baylis-Hillman adducts J Am Chem Soc 122 3534 3535 1:CAS:528:DC%2BD3cXhvVyku7c%3D 10.1021/ja994326n
13. S. Rajesh B. Banerji J. Iqbal 2002 Palladium(0)-catalyzed regioselective synthesis of α-dehydro-β-amino esters from amines and allyl acetates J Org Chem 67 7852 7857 1:CAS:528:DC%2BD38XnsVKms7s%3D 10.1021/jo010981d
14. F. Benfatti G. Cardillo L. Gentilucci E. Mosconi A. Tolomelli 2008 Synthesis of dehydro-β-amino esters via highly regioselective amination of allylic carbonates Org Lett 10 2425 2428 1:CAS:528:DC%2BD1cXmtVaqtrk%3D 10.1021/ol8006919
15. 3 as a water surrogate Tetrahedron Lett 43 9141 9146 1:CAS:528:DC%2BD38Xos1antrw%3D 10.1016/S0040-4039(02)02274-8
16. Y.S. Du X.L. Han X.Y. Lu 2004 Alkaloids-catalyzed regio- and enantioselective allylic nucleophilic substitution of tert-butyl carbonate of the Morita-Baylis-Hillman products Tetrahedron Lett 45 4967 4971 1:CAS:528:DC%2BD2cXksVGit7s%3D 10.1016/j.tetlet.2004.04.135
17. T.Z. Zhang L.X. Dai X.L. Hou 2007 Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2]paracyclophane monophosphines Tetrahedron: Asymmetry 18 1990 1994 1:CAS:528:DC%2BD2sXhtVGitrfO 10.1016/j.tetasy.2007.08.005
18. D.J.V.C.V. Steenis T. Marcelli M. Lutz A.L. Spek J.H.V. Maarseveen H. Hiemstra 2007 Construction of adjacent quaternary and tertiary stereocenters via an organocatalytic allylic alkylation of Morita-Baylis-Hillman carbonates Adv Syn Catal 349 281 286 10.1002/adsc.200600467
19. B.M. Trost D.L.V. Vranken 1996 Asymmetric transition metal-catalyzed allylic alkylations Chem Rev 96 395 422 1:CAS:528:DyaK28XjsVOiuw%3D%3D 10.1021/cr9409804
20. B.M. Trost M.L. Crawley 2003 Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis Chem Rev 103 2921 2943 1:CAS:528:DC%2BD3sXkslens74%3D 10.1021/cr020027w
21. O. Belda C. Moberg 2004 Molybdenum-catalyzed asymmetric allylic alkylations Acc Chem Res 37 159 167 1:CAS:528:DC%2BD3sXpvFKhsbc%3D 10.1021/ar030239v
22. B.M. Trost M.R. Machacek A. Aponick 2006 Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladiumcatalyzed asymmetric allylic alkylation reactions: a working model Acc Chem Res 39 747 760 1:CAS:528:DC%2BD28Xnt12ntL8%3D 10.1021/ar040063c
23. H.L. Cui J. Peng X. Feng W. Du K. Jiang Y.C. Chen 2009 Dual organocatalysis: Asymmetric allylic-allylic alkylation of α,α- dicyanoalkenes and Morita-Baylis-Hillman carbonates Chem Eur J 15 1574 1577 1:CAS:528:DC%2BD1MXhvFKrt7w%3D 10.1002/chem.200802534
24. Jiang K, Peng J, Cui HL, Chen YC. Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates. Chem Commun, 2009, 3955-3957
25. H.L. Cui X. Feng J. Peng K. Jiang Y.C. Chen 2009 Chemoselective asymmetric N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates Angew Chem Int Ed 48 5737 5740 1:CAS:528:DC%2BD1MXoslOrtro%3D 10.1002/anie.200902093
26. X. Feng Y.Q. Yuan H.L. Cui K. Jiang Y.C. Chen 2009 Organocatalytic peroxy- asymmetric allylic alkylation Org Biomol Chem 7 3660 3662 1:CAS:528:DC%2BD1MXhtVGgsLnI 10.1039/b912110b
27. Zhang SJ, Cui HL, Jiang K, Li R, Ding ZY, Chen YC. Enantioselective allylic amination of Morita-Baylis-Hillman carbonates catalysed by modified cinchona alkaloids. Eur J Org Chem, 2009, 5804-5809
28. Z.K. Hu H.L. Cui K. Jiang Y.C. Chen 2010 Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime Sci China Chem 53 1 1309 1313 10.1007/s11426-010-4121-x