Abstract
The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2- O-isopropylidene-3- O-vinyl-glycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4′ carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.
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