An environmentally benign system for synthesis of beta-hydroxyl ketones: L-histidine asymmetrically catalyzed direct aldol reactions in aqueous micelle and water-like media

The first histidine catalyzed direct aldol reactions of ketones with nitrobenzaldehydes in water and in poly(ethylene glycol) (PEG) were reported. It reveals that histidine is a good aldol catalyst for synthesis of beta-hydroxylketones in water and in PEG, giving good to excellent yields of the resp...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 25; no. 3; pp. 356 - 363
Main Authors Peng Yi-Yuan, Peng Shu-Jun, Ding Qiu-Ping, Wang Qi, Cheng Jin-Pei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ROUTE
L-PROLINE
ACID
DE-NOVO SYNTHESIS
AMINO
MICHAEL ADDITION
ALPHA-AMINATION
asymmetric synthesis
poly(ethylene glycol)
beta-hydroxylketone
ORGANOCATALYTIC CONJUGATE ADDITION
SMALL ORGANIC-MOLECULES
histidine
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Summary:The first histidine catalyzed direct aldol reactions of ketones with nitrobenzaldehydes in water and in poly(ethylene glycol) (PEG) were reported. It reveals that histidine is a good aldol catalyst for synthesis of beta-hydroxylketones in water and in PEG, giving good to excellent yields of the respective products. Better enantioand regioselectivity were achieved using low molecular weight PEG as the media. The results show that histidine and PEG-200 or -300 may constitute a promising environmentally benign system for asymmetric synthesis of beta-hydroxylketones.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.200790069