Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction

被引：129

作者：

Balan, D ^{[1
]}

Adolfsson, H ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(03)00289-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral quinuclidine derivatives were employed as catalysts in the one-pot, three-component aza-Baylis-Hillman reaction between arylaldehydes, tosylamide and alkyl acrylates or acrylonitrile. A sterically non-hindered tricyclic derivative of quinidine was found to be the most efficient catalyst in transferring its chiral information. High conversions were ensured by using a catalytic amount of titanium isopropoxide and by the addition of molecular sieves (4 A). The adducts formed, alpha-methylene-beta-amino acid derivatives, were obtained in good yields (up to 95%) and in enantioselectivities up to 74%. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2521 / 2524

页数：4

共 28 条

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