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题名: An unexpected inversion of enantioselectivity in direct asymmetric aldol reactions on a unique L-proline/gamma-Al2O3 catalyst
作者: Zhong, Lin;  Xiao, Hanliang;  Li, Can
关键词: asymmetric catalysis ;  aldol reactions ;  L-proline/gamma-Al2O3 catalyst ;  inversion ;  enantioselectivity
刊名: JOURNAL OF CATALYSIS
发表日期: 2006-10-25
DOI: 10.1016/j.jcat.2006.07.025
卷: 243, 期:2, 页:442-445
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences ;  Technology
类目[WOS]: Chemistry, Physical ;  Engineering, Chemical
研究领域[WOS]: Chemistry ;  Engineering
英文摘要: L-proline adsorbed on gamma-Al2O3 unexpectedly switches the enantioselectivity of the direct asymmetric aldol reaction of acetone with p-nitrobenzaldehyde from 68% ce (R configuration for free L-proline catalyst) with 80% yield to 21% ee (S configuration) with 78% yield. The inversion of enantioselectivity was also observed in the direct asymmetric aldol reactions of acetone with several other aromatic aldehydes catalyzed by the L-proline adsorbed on gamma-Al2O3. This inversion phenomenon is found to be general for different types of amino acids adsorbed on gamma-Al2O3. The hydroxyl groups on gamma-Al2O3 are found to be involved in the inversion induction of enantioselectivity in these direct asymmetric aldol reactions. (c) 2006 Elsevier Inc. All rights reserved.
关键词[WOS]: CHIRAL CATALYST ;  METAL-SURFACES ;  AMINO-ACIDS ;  HYDROGENATION ;  PROLINE ;  PLATINUM ;  ALUMINA ;  KETOPANTOLACTONE ;  ORGANOCATALYST ;  CINCHONIDINE
语种: 英语
WOS记录号: WOS:000241591900025
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140281
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
2.Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

Recommended Citation:
Zhong, Lin,Xiao, Hanliang,Li, Can. An unexpected inversion of enantioselectivity in direct asymmetric aldol reactions on a unique L-proline/gamma-Al2O3 catalyst[J]. JOURNAL OF CATALYSIS,2006,243(2):442-445.
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