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Synfacts 2011(12): 1319-1319  
DOI: 10.1055/s-0031-1289385
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

A Simplified Catalytic System for Direct Asymmetric Aldol Reaction of Thioamides

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Y. Kawato, M. Iwata, R. Yazaki, N. Kumagai*, M. Shibasaki*
Institute of Microbial Chemistry, Tokyo and The University of Tokyo, Japan
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

This work describes the development of a second-generation catalytic system for the direct asymmetric aldol reaction of thioamides. The first-generation system was reported by Shibasaki and Kumagai (J. Am. Chem. Soc. 2009, 131, 18244; Synfacts 2010, 316) and consisted of [Cu(MeCN)4]PF6/1/LiOAr (ArOH = 2,2,5,7,8-pentamethylchromanol). The new simplified system includes mesitylcopper and 1 only, which eliminated the need of the tedious preparation of lithium aryloxide. The new catalyst was applied to a concise enantioselective synthesis of atorvastatin (widely known as Lipitor®).