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Asymmetric Synthesis of Chiral 1,3‐Diaminopropanols: Bisoxazolidine‐Catalyzed CC Bond Formation with α‐Keto Amides
Author(s) -
Xu Hanhui,
Wolf Christian
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105778
Subject(s) - catalysis , ligand (biochemistry) , chemistry , combinatorial chemistry , nitroaldol reaction , enantioselective synthesis , stereochemistry , organic chemistry , biochemistry , receptor
Three high‐yielding steps lead to the formation of chiral 1,3‐diaminopropanols from aliphatic and aromatic α‐keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO 2 CF 3 ) 2 and the bisoxazolidine ligand L1 , is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.