The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions

被引：80

作者：

Aggarwal, VK ^{[1
]}

Castro, AMM ^{[1
]}

Mereu, A ^{[1
]}

Adams, H ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(02)00021-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrophilic behaviour of enantiomerically pure N-p-toluenesulfinimines (1a, d) adn N-tert-butanesulfinimine 2 has been tester in the asymmetric Baylis-Hillman reaction with methyl acrylate with and without Lewis acids. In the presence of In(OTf)(3) good yields and high diastereoselectives have been achieved providing an effective route to beta-amino-alpha-methylene esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1577 / 1581

页数：5

共 39 条

[1] Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated
Aggarwal, VK
Dean, DK
Mereu, A
Williams, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) : 510 - 514
[2] Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications
Aggarwal, VK
Mereu, A
[J]. CHEMICAL COMMUNICATIONS, 1999, (22) : 2311 - 2312
[3] Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction
Aggarwal, VK
Mereu, A
Tarver, GJ
McCague, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) : 7183 - 7189
[4] [Anonymous], TETRAHEDRON-ASYMMETR
[5] Selective formation of α-methylene-β-amino acid derivatives through the aza version of the Baylis-Hillman reaction
Balan, D
Adolfsson, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) : 6498 - 6501
[6] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[7] A novel isoxazole-based scaffold for combinatorial chemistry
Batra, S
Rastogi, SK
Kundu, B
Patra, A
Bhaduri, AP
[J]. TETRAHEDRON LETTERS, 2000, 41 (31) : 5971 - 5974
[8] PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES
BERTENSHAW, S
KAHN, M
[J]. TETRAHEDRON LETTERS, 1989, 30 (21) : 2731 - 2732
[9] A simple, mild synthesis of 3-aryl-2-methylidene-3-(p-tolylsulfonylamino)propanoates
Campi, EM
Holmes, A
Perlmutter, P
Teo, CC
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (09) : 1535 - 1540
[10] Ciganek E., 1997, ORG REACTIONS, V51, P201

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