ASYMMETRIC INDUCTION IN [2+2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO 1,2-O-ISOPROPYLIDENE-5-O-VINYL-D-GLYCOFURANOSES

被引：0

作者：

KALUZA, Z

FURMAN, B

CHMIELEWSKI, M

机构：

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 07期

关键词：

D O I：

暂无

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-5-O-vinyl-D-glycofuranoses is presented. The stereoselectivity strongly depends on substitution and configuration at the C-3 carbon atom. A small substituent at C-3 or allo configuration of the sugar promote excellent stereoselectivity, affording (s) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 20, 22-26, and 31 provides the respective clavams 32-38.

引用

页码：1719 / 1730

页数：12

共 4 条

[1] 5-DEOXY-5-ALKYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLOFURANOSES AS CHIRAL AUXILIARIES IN ASYMMETRIC 1,4-ADDITION REACTION [J].