title: A Convergent Strategy for the Asymmetric Synthesis of Enantiomerically Pure Bicyclic Compounds by Using a Silicon-Directed Cycloaddition Reaction: The Synthesis of Enantiomerically Pure Bicyclo
abstract: An asymmetric allylmetalation followed by a silicon-stereodirected cycloaddition gives enantiomerically pure bicyclic compounds. The synthesis of enantiopure 1 (see scheme) in a yield of 65-74 %, 93 % ee, and >98 % de provides an illustration of the efficacy of the method. The preferential formation of 1 rather than its diastereoisomer (32:1), during the cycloaddition step, matches the result predicted by RHF and density functional theory studies.
authors.affiliation: Laboratoire de Chimie Organique de Synthèse, Université catholique de Louvain, place L. Pasteur 1, B-1348 Louvain-la-Neuve (Belgium).
authors.initials: JM
authors.lastname: Adam
authors.initials: L
authors.lastname: Ghosez
authors.initials: KN
authors.lastname: Houk