Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives
Organic Letters2011Vol. 14(1), pp. 146–149
Citations Over TimeTop 10% of 2011 papers
Abstract
Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with SmI(2)-H(2)O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.
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