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Synfacts 2005(0): 0069-0069  
DOI: 10.1055/s-2005-869929
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Germanium(II)-Mediated Cross-Aldol Reac­-tion between Aldehydes and Bromoaldehydes

Contributor(s): Paul Knochel, Andrei Gavryushin
M. Yasuda, S. Tanaka, A. Baba*
Osaka University, Japan
Reductive Cross-Aldol Reaction Using Bromoaldehyde and an Aldehyde Mediated by Germanium(II): One-Pot, Large-Scale Protocol
Org. Lett.  2005,  7:  1845-1848  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

aldols - bromoaldehydes - germanium

Significance

This is the first example of the reaction between an aldehyde, α-haloaldehyde and a reducing agent, leading to the aldol-type product. The high instability of the β-hydroxyaldehyde products prevents the application of usual low-­valent metal like tin or chromium. The method is convenient and can be easily scaled up.

Comment

An aldol-like reaction between α-bromoaldehyde and an aldehyde, thus avoiding self-aldol reactions, is an excellent alternative for the conventional aldol synthesis. The problem so far was the choice of the proper reducing agent to form the enolate from the haloaldehyde. Further investigation in this field will certainly allow performing the reaction diastereo- and enantioselectively.

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