Catalytic Generation of Indium Hydride in a Highly Diastereoselective Reductive Aldol Reaction

A one‐pot synthesis of β‐hydroxyketones has been achieved by the reductive aldol reaction of enones and aldehydes in the presence of Et3SiH and a catalytic amount of InBr3 (see scheme). The reaction is highly diastereoselective and no reduction of the starting aldehydes occurs. This method is superi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-01, Vol.43 (6), p.711-714
Main Authors: Shibata, Ikuya, Kato, Hirofumi, Ishida, Tatsuya, Yasuda, Makoto, Baba, Akio
Format: Article
Language:English
Subjects:
aldol reaction
diastereoselectivity
hydroxyketones
indium
silanes
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Summary:A one‐pot synthesis of β‐hydroxyketones has been achieved by the reductive aldol reaction of enones and aldehydes in the presence of Et3SiH and a catalytic amount of InBr3 (see scheme). The reaction is highly diastereoselective and no reduction of the starting aldehydes occurs. This method is superior to conventional reductive aldol reactions in terms of applicability to a wide range of enones and aldehydes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352738