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Diastereoselective Reductive Amination of Aryl Trifluoromethyl Ketones and α‐Amino Esters
Author(s) -
Hughes Greg,
Devine Paul N.,
Naber John R.,
O'Shea Paul D.,
Foster Bruce S.,
McKay Daniel J.,
Volante R. P.
Publication year - 2007
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.200603745
Subject(s) - diastereomer , reductive amination , chemistry , imine , trifluoromethyl , stereoselectivity , amination , aryl , hydroamination , benzylamine , stereochemistry , organic chemistry , catalysis , alkyl
Reductionist art : Careful choice of the reducing agent in the reductive amination of trifluoromethyl ketones with α‐amino esters allows stereoselective access, from the imine formed, to either the R , S or S , S diastereomers of the resulting amino acids. Whereas NaBH 4 affords the R , S diastereomers, Zn(BH 4 ) 2 affords the S , S diastereomers (see scheme), which can be easily converted into potent cathepsin K inhibitors.
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