Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines (thiooxime S-oxides)

被引：20

作者：

Li, GG ^{[1
]}

Wei, HX ^{[1
]}

Hook, JD ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(99)00756-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (alpha-carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et2O-CH2Cl2). This new system has made it possible to utilize those p-toluenesulfinimines of low solubility in Et2O as the electrophiles to react with anionic (alpha-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding beta-mono and beta,beta-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4611 / 4614

页数：4

共 24 条

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