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Synfacts 2007(5): 0495-0495  
DOI: 10.1055/s-2007-968450
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Monoacetylation of Prochiral Amino-2-alkyl-1,3-propanediols

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Honjo, M. Nakao, S. Sano, M. Shiro, K. Yamaguchi, Y. Sie, Y. Nagao*
The University of Tokushima, Rigaku Corporation, Tokyo and Tokushima Bunri University, Kagawa, Japan
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The authors report a non-enzymatic approach to monoacetylation of prochiral diols giving 70-88% ee. They utilize a chiral sulfon­amide-Zn complex as catalyst. The use of Trost’s catalyst for the monobenzoylation of pro­chiral 1,3-diols was attempted (B. M. Trost, T. Mino J. Am. Chem. Soc. 2003, 125, 2410-2411) but gave only 10% ee. The difficulty is believed to be due to the presence of the quaternary prochiral center. The use of the Zn-bridged bis(sulfonamide) catalyst proved to be efficacious for this reaction.