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Stereoselective Synthesis of Boc‐Protected cis and trans ‐4‐Trifluoromethylprolines by Asymmetric Hydrogenation Reactions
Author(s) -
Del Valle Juan R.,
Goodman Murray
Publication year - 2002
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 - 10.1002/1521-3773(20020503)41:9<1600::aid-anie1600>3.0.co;2-v
Subject(s) - diastereomer , stereoselectivity , steric effects , asymmetric hydrogenation , chemistry , proline , catalytic hydrogenation , trifluoromethyl , stereoisomerism , cis–trans isomerism , stereochemistry , noyori asymmetric hydrogenation , organic chemistry , enantioselective synthesis , amino acid , catalysis , biochemistry , alkyl
Stereocontrolled synthesis of cis and trans ‐substituted prolines by a divergent approach, leads to the preparation of cis ‐(4 S )‐ and trans ‐(4 R )‐trifluoromethyl‐ L ‐proline from hydroxyproline. The key pyrroline intermediates were subjected to hydrogenation (see scheme; A=sterically directed hydrogenation, B=hydroxy‐directed hydrogenation; Boc= tert ‐butoxycarbonyl, TBS= tert ‐butyldimethylsilyl), to afford products in high diastereomeric excess.