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
收藏
页码：3307 / 3310
页数：4
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