Abstract
The asymmetric[2+2]cycloaddition of chlorosulfonyl isocyanate to Z and E3-O-butyl-1′-enyl-1, 2-O-isopropylidene-5-O-trityl-α- d-xylofuranoses proceeds with excellent stereoselectivity affording cis azetidinone 12 from cis olefin and trans azetidine 13 from trans olefin, whereas in both cases r 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. [Display omitted]
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