STEREOCONTROLLED CONSTRUCTION OF 3-SULFENYLAZETIDIN-2-ONES

被引：15

作者：

FUJISAWA, T

SATO, D

SHIMIZU, M

机构：

[1] Department of Chemistry for Materials, Mie University, Tsu, Mie

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(01)80952-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Diastereoselective addition reaction of the enolate of alpha-sulfenylacetates to a chiral imine possessing a (4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolane ring as a chiral auxiliary could be regulated by the enolate metals and the substituents on die sulfur atom. Addition of the titanium enolates provided (3R,4R)-beta-lactams exclusively, while the corresponding (3R,4S)-beta-lactam was obtained predominantly by the condensation using the zinc enolate of t-butyl alpha-methylthioacetate with the chiral imine.

引用

页码：2343 / 2346

页数：4

共 22 条

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