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Synfacts 2011(3): 0293-0293  
DOI: 10.1055/s-0030-1259488
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Halogenotin Hydride Catalyzed Diastereoselective Reductive Aldol Reaction

Contributor(s): Hisashi Yamamoto, Patrick Brady
I. Shibata*, S. Tsunoi, K. Sakabe, S. Miyamoto, H. Kato, H. Nakajima, M. Yasuda, A. Baba
Osaka University, Japan
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Publikationsdatum:
16. Februar 2011 (online)

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Significance

A reductive aldol reaction of enones to ketones is described. The reaction is catalyzed by dibutylhalgenotin hydride and employs diphenylsilane as the stoichiometric reductant. The reaction is applicable to a number of carbonyl compounds, including aldehydes, ketones, α-keto esters, α-alkoxy ketones and α-halo ketones. Tertiary carbinols can be obtained with high syn selectivity.