P. Merino, T. Tejero, A. Diez-Martinez
Nov 1, 2011
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Influential Citations
14
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Journal
European Journal of Organic Chemistry
Abstract
An efficient methodology for the synthesis of all-cis-N-hydroxypyrrolidines has been developed through the formal [3+2] dipolar cycloaddition of electron-poor alkenes and nitrone ylides generated from N-(methoxycarbonylmethyl)nitrones. Treatment of the nitrone with a tertiary amine in the presence of either a lithium salt or butyllithium followed by addition of the alkene at low temperature provided the product in very good chemical yield and excellent diastereoselectivity. Isolation and characterization of a key intermediate demonstrated that the reaction is a stepwise process consisting of an initial Michael addition followed by an intramolecular Mannich-type reaction.