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Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol

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Chinese Chemical Letters 2010年第3期21卷 309-311页

作者： Geng Xu[a] Zhan Zhu Liu[a] [a] Key Laboratory of Bioactive Substances Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College) Ministry of Education. Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050 China

A highly effective,new chiral 1,2,3,4-tetrahydroisoquinoline catalyst 1 for the diethylzinc addition to aryl aldehydes has been *** 10 mol%of this chiral catalyst,secondary alcohols can be obtained in up to 87%yield a... 详细信息

关键词： β-amino alcohol Tetrahydroisoquinoline Diethylzinc Asymmetric addition

Synthesis of new chiral 1,2,3,4-tertrahydroisoquinoline β-amino alcohol for asymmetric diethylzinc addition to aryl aldehydes(Ⅰ)

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Chinese Chemical Letters 2009年第12期20卷 1393-1396页

作者： Geng Xu Zhan Zhu Liu Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College) Ministry of Education Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050 China

Four new chiral 1,2,3,4-tetrahydroisoquinoline-derived G-amino alcohols were synthesized from commercially available LDOPA. These ligands were evaluated in the asymmetric addition of diethylzinc to benzaldehydes and showed different catalytic activities （up to 86% ee）. The solvent played an important role in the enantioselective process. The transition state models were proposed to explain the reversion of the product configuration.

关键词： β-amino alcohol Tetrahydroisoquinoline Diethylzinc Asymmetric addition

Synthesis of new chiral 1,2,3,4-tetrahydroisoquinoline β-amino alcohols from L-DOPA

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Chinese Chemical Letters 2008年第11期19卷 1271-1273页

作者： Geng Xu Zhan Zhu Liu Institute of Materia Medica Peking Union Medical College ＆ Chinese Academy of Medical Science Beijing 100050 China

Four new chiral 1,2,3,4-tetrahydroisoquinoline-derived β-amino alcohols were synthesized from L-DOPA in good yields. The structures of the target compounds were confirmed by ^1H NMR, ^13C NMR and MS.

关键词： β-amino alcohol Tetrahydroisoquinoline L-DOPA Pictet-Spengler reaction

Enantioselective addition of Et_2Zn to aldehydes catalyzed by chi-ral aliphatic β-amino alcohols

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Chinese Journal of Chemistry 2000年第4期18卷 582-584页

作者：沈宗旋许学农刘小峰张丽芬张雅文 Department of Chemistry and Chemical Engineering Suzhou University Suzhou Jiangsu 215006 China

This paper describes the preparation of two new optically active aliphatic β-amino alcohols (R)-5,5-dimethyl-2-(dimethy-lamino)-1,1-diphenyl-1-hexanol (1a) and (S)-8,8-dimethyl-2-(dimethylamino)-1, 1-diphenyl-1-nonanol (1b). They were synthesized by methylation of the corresponding β-amino alcohols 2a and 2b. Compounds la and 1b catalyze the addition of diethylzinc to various aldehydes enantioselectively. The catalyst structure-enantioselectivity relationships were discussed.

关键词： Enantioselective addition β-amino alcohol enan-tioselectivity