Section 46
Chapter 45,029

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

Adam; Ghosez; Houk

Angewandte Chemie 38(18): 2728-2730


ISSN/ISBN: 1433-7851
PMID: 10508362
DOI: 10.1002/(sici)1521-3773(19990917)38:18<2728::aid-anie2728>3.0.co;2-0
Accession: 045028111

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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.

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