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
Org. Lett., 2005, 7 (9), pp 1845–1848
DOI: 10.1021/ol050533i
Publication Date (Web): March 25, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, yasuda@chem.eng.osaka-u.ac.jp

Abstract

Abstract Image

The reaction of α-bromoaldehyde with aldehyde in the presence of GeCl2−dioxane gave the syn-selective cross-aldol equivalent. A catalytic amount of Bu4NBr improved the yield and selectivity. The initially formed aldol adduct (β-germoxyaldehyde) did not suffer from over-reaction. This system enabled an intramolecular aldol reaction to give cyclic compounds effectively. One-pot synthetic methodology including bromination of aldehyde followed by cross-aldol reaction with the second aldehyde was successful on a large-scale.

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History

  • Published In Issue April 28, 2005
  • Received March 11, 2005

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