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In Situ Formed Bifunctional Primary Amine–Imine Catalyst for Asymmetric Aldol Reactions of α‐Keto Esters
Author(s) -
Zhu Xi,
Lin Aijun,
Fang Ling,
Li Wei,
Zhu Chengjian,
Cheng Yixiang
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100200
Subject(s) - bifunctional , imine , amine gas treating , aldol reaction , chemistry , primary (astronomy) , catalysis , organic chemistry , hydrolysis , aryl , alkyl , combinatorial chemistry , astronomy , physics
In prime condition : The hydrolysis of a chiral diimine precursor can be carried out by a Brønsted acid to form an in situ primary amine–imine intermediate as a bifunctional primary aminocatalyst, which promoted direct asymmetric aldol reactions between α‐keto esters and ketones in high yields (up to 88 %) and with excellent enantioselectivities (see scheme; R 1 , R 2 , R 4 =alkyl; R 3 =aryl).