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The Mimic of Type II Aldolases Chemistry: Asymmetric Synthesis of β ‐Hydroxy Ketones by Direct Aldol Reaction
Author(s) -
Lu Zhijin,
Mei Haibo,
Han Jianlin,
Pan Yi
Publication year - 2010
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2010.00998.x
Subject(s) - aldol reaction , aldolase a , ketone , chemistry , trifluoromethanesulfonate , catalysis , zinc , enantioselective synthesis , combinatorial chemistry , organic chemistry , enzyme
An efficient direct aldol reaction has been developed for the synthesis of chiral β ‐hydroxy ketone using a combination of C 1 ‐symmetric chiral prolinamides based on o ‐phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts.