Tetrahedron

Enantioselective homoallyl-cyclopropanation of dibenzylideneacetone by modified allylindium halide reagents—rapid access to enantioenriched 1-styryl-norcarene

GC Lloyd-Jones, PD Wall, JL Slaughter, AJ Parker…

Index: Lloyd-Jones, Guy C.; Wall, Philip D.; Slaughter, Jennifer L.; Parker, Alexandra J.; Laffan, David P. Tetrahedron, 2006 , vol. 62, # 49 p. 11402 - 11412

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Citation Number: 14

Abstract

Dibenzylideneacetone (8) reacts with in situ-generated allylindium halide reagents to yield the product of a homoallyl-cyclopropanation reaction: 2-(3 ″-butenyl)-1, 1-bis [(E)-2′- phenylethenyl] cyclopropane (9), which proceeds via step-wise cleavage of the CO bond and delivery of two allyl fragments from the reagent. A range of enantiomerically enriched ligands have been tested as stoichiometric asymmetric modifiers for this process. ...