Reductive Cross-Aldol Reaction Using Bromoaldehyde and an Aldehyde Mediated by Germanium(II): One-Pot, Large-Scale Protocol

Makoto Yasuda, Shin-ya Tanaka and Akio Baba*

*Department of Molecular Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: yasudachem.eng.osaka-u.ac.jp

M. Yusada, S.-Y. Tanaka, A. Baba, Org. Lett., 2005, 7, 1845-1848.

DOI: 10.1021/ol050533i

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Abstract

The reaction of α-bromoaldehydes with aldehydes in the presence of GeCl₂-dioxane gave cross-aldol equivalents with syn-selectivity. The initially formed β-germoxyaldehydes did not lead to side products. Addition of a catalytic amount of Bu₄NBr improved the yield and selectivity.

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Key Words

Reductive Cross Aldol Reactions, β-Hydroxy Ketones

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ID: J54-Y2005-520