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Synthesis 2010(5): 811-817  
DOI: 10.1055/s-0029-1218619
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Optically Active β-Amino Alcohols by Asymmetric Transfer Hydrogenation of α-Amino Ketones

Zhou Xu*a, Songlei Zhua, Yongmin Liua, Ling Hea, Zhicong Gengb, Yawen Zhang*b
a Department of Chemistry, Xuzhou Medical College, Xuzhou 221004, P. R. of China
Fax: +86(512)65880340; e-Mail: xuzhou8111@yahoo.com.cn;
b Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Suzhou (Soochow) University, Suzhou 215123, P. R. of China
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Publikationsverlauf

Received 24 September 2009
Publikationsdatum:
22. Dezember 2009 (online)

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Abstract

A number of optically active amino alcohols were synthesized by direct asymmetric transfer hydrogenation of the corresponding amino ketones with good-to-high enantiomeric excesses (up to 95%) and excellent yields (up to 93% ). When the range of substrates was broadened to include α-sulfonamido ketones or α-keto sulfones, the corresponding products were obtained with 100% enantiomeric excesses. The absolute configuration of (1R)-2-[(4-chlorophenyl)amino]-1-(4-methoxyphenyl)ethanol was confirmed by X-ray crystal structure analysis.

Key words

amino alcohols - amino ketones - hydrogenations - stereo­selective synthesis - aziridines