Application of the retroaldol reaction to asymmetric synthesis: a new concept in organic syntheses

Aldol 5b, easily obtained from dihydrocarvone 6b, reacts with organolithium and Grignard reagents leading to enantiomerically enriched alcohols 8 (ee up to 35%). Thus, aldol 5b is a synthetic equivalent of benzaldehyde with a masked prochiral face.

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-03, Vol.10 (6), p.1015-1018
Main Authors: Quesnel, Yannick, Toupet, Loı̈c, Duhamel, Lucette, Duhamel, Pierre, Poirier, Jean-Marie
Format: Article
Language:English
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Summary:Aldol 5b, easily obtained from dihydrocarvone 6b, reacts with organolithium and Grignard reagents leading to enantiomerically enriched alcohols 8 (ee up to 35%). Thus, aldol 5b is a synthetic equivalent of benzaldehyde with a masked prochiral face.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00093-2