STEREOCHEMICAL COURSE OF SOPROPYLIDENE-ALPHA-D-XYLOFURANOSE(2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO CIS AND TRANS 3)

Authors
FURMAN B KALUZA Z CHMIELEWSKI M
Citation
B. Furman et al., STEREOCHEMICAL COURSE OF SOPROPYLIDENE-ALPHA-D-XYLOFURANOSE(2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO CIS AND TRANS 3), Tetrahedron, 52(16), 1996, pp. 6019-6024
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
16
Year of publication
1996
Pages
6019 - 6024
Database
ISI
SICI code
0040-4020(1996)52:16<6019:SCOS>2.0.ZU;2-7
Abstract
The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to Z an d E -O-isopropylidene-5-O-trityl-alpha-D-xylofuranoses proceeds with e xcellent stereoselectivity affording cis azetidinone 12 from cis olefi n and trans azetidine 13 from trans olefin, whereas in both cases a co nfiguration is induced at C-4' of the azetidin-2-one ring. Intramolecu lar cyclization of azetidinones 16 and 17 affords respective diasterom eric cephams 18 and 19. Copyright (C) 1996 Elsevier Science Ltd