Abstract
Aziridination of α,β-unsaturated amides was effected by treatment with lithiated 3,3-pentamethylenediaziridine in high diastereoselectivity. cis -Aziridine was the predominant diastereomer irrespective of the geometry of the substrates. A stepwise mechanism, 1,4-addition of a lithiated diaziridine to α,β-unsaturated amides and subsequent ring closure at the nitrogen atom, was proposed to explain the unusual cis -selectivity. Aziridination of α,β-unsaturated amides was effected by treatment with lithiated 3,3-pentamethylenediaziridine in high cis -stereoselectivity.
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