Construction of C-S bonds with a quaternary stereocenter through a formal Michael reaction:: Asymmetric synthesis of tertiary thiols

被引：34

作者：

Palomo, C

Oiarbide, M

Dias, F

López, R

Linden, A

机构：

[1] Univ Basque Country, Fac Quim, Dept Quim Organ 1, E-20080 San Sebastian, Spain

[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 25期

关键词：

asymmetric synthesis; chirality; Lewis acids; Michael addition; thiols;

D O I：

10.1002/anie.200453889

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).

引用

页码：3307 / 3310

页数：4

共 46 条

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