Solvent-dependent diastereoselectivities in reductions of beta-hydroxyketones by SmI2.
Org Lett
; 6(16): 2685-8, 2004 Aug 05.
Article
em En
| MEDLINE
| ID: mdl-15281744
ABSTRACT
The reductions of a series of beta-hydroxyketones by SmI(2) were examined in THF, DME, and CH(3)CN using methanol as a proton source. Reductions in THF and DME typically lead to the syn diastereomer with DME providing higher diastereoselectivities. Reductions in CH(3)CN provided the anti diastereomer predominantly. This study reveals that solvation plays an important role in substrate reduction by SmI(2). [reaction see text]
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2004
Tipo de documento:
Article
País de afiliação:
Estados Unidos