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An Environmentally Benign System for Synthesis of β ‐Hydroxylketones: L ‐Histidine Asymmetrically Catalyzed Direct Aldol Reactions in Aqueous Micelle and Water‐like Media
Author(s) -
Peng YiYuan,
Peng ShuJun,
Ding QiuPing,
Wang Qi,
Cheng JinPei
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790069
Subject(s) - chemistry , aldol reaction , ethylene glycol , peg ratio , micelle , aqueous medium , histidine , catalysis , regioselectivity , aqueous solution , organic chemistry , combinatorial chemistry , enzyme , finance , economics
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 β ‐hydroxylketones in water and in PEG, giving good to excellent yields of the respective products. Better enantio‐ and 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 β ‐hydroxylketones.