title: Radical cyclization cascades of unsaturated Meldrum's acid derivatives.
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.
authors: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
authors: Brice
authors: B
authors: Sautier
authors: Sarah E
authors: SE
authors: Lyons
authors: Michael R
authors: MR
authors: Webb
authors: David J
authors: DJ
authors: Procter
mesh_terms: D003500:Cyclization; D004146:Dioxanes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004146:Dioxanes; C076489:Meldrum's acid