Unusual Reagent Control of Diastereoselectivity in the 1,2-Addition of Hard Carbon Nucleophiles to C6-Heteroatom Substituted Cyclohexenones

A surprising and synthetically useful counterion-dependent reversal of diastereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C6-heterosubstituted cyclohexenones. In general, Grignard reagents added syn to the C6-substituent and Li reagents added anti, although some exception...

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Bibliographic Details
Published in:Organic letters 2001-12, Vol.3 (25), p.4007-4010
Main Authors: Lindsay, Harriet A, Salisbury, Catherine L, Cordes, Wally, McIntosh, Matthias C
Format: Article
Language:English
Online Access:Get full text
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Summary:A surprising and synthetically useful counterion-dependent reversal of diastereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C6-heterosubstituted cyclohexenones. In general, Grignard reagents added syn to the C6-substituent and Li reagents added anti, although some exceptions were found. Selectivities could be increased in some cases by appropriate choice of solvent and/or cosolvent.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016673j