Volume 19, Issue 11 pp. 1130-1135
Article
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Asymmetric reduction of aminoketones with borane and chiral oxazaborolidine catalyst

Ya-Wen Zhang

Ya-Wen Zhang

Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China

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Zong-Xuan Shen

Zong-Xuan Shen

Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China

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Hong-Bing Qin

Hong-Bing Qin

Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China

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Yong-Hua Li

Yong-Hua Li

Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu 215006, China

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Kai-Bei Yu

Kai-Bei Yu

Analysis Center, Chengdu Branch of the Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

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First published: 26 August 2010
Citations: 4

Abstract

A group of α- and β-N, N-dialkyl amino ketones were reduced enantioselectively by 2 moles of borane-tetrahydrofuran in the presence of 10 mol% of the in-situ formed chiral oxazaborolidine, followed by diluted hydrochloric acid. The resulting amino alcohol-borane complexes were treated with hydrogen chloride-glycol-methanol to give the optically active amino alcohol with the ee up to 99%.

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