Stereochemical course of [2+2]cycloaddition of chlorosulfonyl isocyanate to cis and trans 3-O-but-1'-enyl-1,2-O-isopropylidene-alpha-D-xylofuranose

被引：17

作者：

Furman, B

Kaluza, Z

Chmielewski, M

机构：

[1] Institute of Organic Chemistry, Polish Academy of Sciences

来源：

TETRAHEDRON | 1996年 / 52卷 / 16期

关键词：

D O I：

10.1016/0040-4020(96)00239-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to Z and E 3-O-butyl-1'-enyl-1,2-O-isopropylidene-5-O-trityl-alpha-D-xylofuranoses proceeds with excellent stereoselectivity affording cis azetidinone 12 from cis olefin and trans azetidine 13 from trans olefin, whereas in both cases a configuration is induced at C-4' of the azetidin-2-one ring. Intramolecular cyclization of azetidinones 16 and 17 affords respective diasteromeric cephams 18 and 19. Copyright (C) 1996 Elsevier Science Ltd

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页码：6019 / 6024

页数：6

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