Dramatic solvent effect on the diastereoselectivity of Michael addition: study toward the synthesis of the ABC ring system of hexacyclinic acid.
Org Lett
; 10(1): 45-8, 2008 Jan 03.
Article
em En
| MEDLINE
| ID: mdl-18052183
ABSTRACT
During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we have observed a dramatic influence of the solvent on both our key steps. The diastereoselectivity of the intermolecular Michael addition could be totally reversed by changing the polarity of the solvent, and trifluoroethanol was found to be the optimal solvent for the following Mn(III)-promoted radical cyclization.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Heterocíclicos de 4 ou mais Anéis
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article