Synlett 2007(11): 1720-1724  
DOI: 10.1055/s-2007-982560
LETTER
© Georg Thieme Verlag Stuttgart · New York

Germanium(II)-Mediated Reductive Cross-Aldol Reaction of Aldehydes: Synthesis of Aldols with Diastereocontrolled Quaternary Carbon Centers

Shin-ya Tanaka, Makoto Yasuda, Akio Baba*
Department of Applied Chemistry, Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
e-Mail: baba@chem.eng.osaka-u.ac.jp;
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Publikationsverlauf

Received 3 April 2007
Publikationsdatum:
25. Juni 2007 (online)

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Abstract

anti-Selective synthesis of aldols with quaternary carbon centers was achieved by germanium(II)-mediated reductive cross-aldol reaction of tertiary α-bromo aldehydes with both aromatic and aliphatic aldehydes. One-pot direct reduction and reductive amination of the aldol products were performed to give the corresponding 1,3-diol and 1,3-amino alcohol with stereocontrolled quaternary carbon centers.