Unusual reagent control of diastereoselectivity in the 1,2-addition of hard carbon nucleophiles to C(6)-heteroatom substituted cyclohexenones.
Org Lett
; 3(25): 4007-10, 2001 Dec 13.
Article
em En
| MEDLINE
| ID: mdl-11735571
ABSTRACT
[reaction see text] A surprising and synthetically useful counterion-dependent reversal of diastereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C(6)-heterosubstituted cyclohexenones. In general, Grignard reagents added syn to the C(6)-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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Hidrocarbonetos Cíclicos
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2001
Tipo de documento:
Article
País de afiliação:
Estados Unidos