Asymmetric synthesis of vicinal thioether alcohols by diastereoselective 1,2-addition of carbon nucleophiles to enantiomerically enriched alpha-sulfenylated aldehydes

被引：27

作者：

Enders, D

Piva, O

Burkamp, F

机构：

[1] Institut für Organische Chemie, Rheinisch-Westfälische TH, D-52074 Aachen

来源：

TETRAHEDRON | 1996年 / 52卷 / 08期

关键词：

D O I：

10.1016/0040-4020(95)01040-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active alpha-sulfenylated aldehydes (S)-1, readily available by asymmetric alkylation of alpha-sulfenylated acetaldehyde-SAMP-hydrazones followed by chemoselective oxidative removal of the chiral auxiliary, can be transformed into vicinal thioether alcohols 2, 5 and 6 by diastereoselective 1,2-addition using various carbon nucleophiles. The final compounds are obtained with high enantiomeric- (ee = 80 - 97%) and diastereomeric excesses (de = 88 - > 95%) in good chemical yields (51 - 88%).

引用

页码：2893 / 2908

页数：16

共 44 条

[1] CARBENOID TYPE BASE INDUCED RING EXPANSION OF THE ADDUCTS OF CYCLIC-KETONES WITH BIS(PHENYLTHIO)METHYLLITHIUM [J].