Synlett 2004(13): 2443-2444  
DOI: 10.1055/s-2004-834808
CLUSTER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Reduction-Aldol Reaction of Esters

Mikio Sasaki, Andrei K. Yudin*
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada
e-Mail: ayudin@chem.utoronto.ca;
Further Information

Publication History

Received 27 July 2004
Publication Date:
07 October 2004 (online)

Abstract

We have developed a new protocol for making aldol adducts in a one-pot reaction between esters and silyl enol ethers in the presence of DIBALH without isolating the intermediate aldehydes. Lewis acid activation of the initially formed aluminated hemiacetals produces highly reactive electrophilic aldehyde equivalents in situ. Using this protocol, various aldol adducts can be readily obtained in up to 90% yield on a large scale.

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