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, Christophe;Ghosez, Léon;Houk
(1999) Angewandte Chemie — Vol. 38, n° 18, p. 2728-2730 (1999)

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  • Adam, ChristopheUCLouvain
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  • Ghosez, LéonUCLouvain
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  • Houk
    Author
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.
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Adam, C., Ghosez, L., & Houk. (1999). 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. Angewandte Chemie, 38(18), 2728-2730. https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18<2728::AID-ANIE2728>3.0.CO;2-0 (Original work published 1999)