Premium
Asymmetric Hydrogenation of Pyridinium Salts with an Iridium Phosphole Catalyst
Author(s) -
Chang Mingxin,
Huang Yuhua,
Liu Shaodong,
Chen Yonggang,
Krska Shane W.,
Davies Ian W.,
Zhang Xumu
Publication year - 2014
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.201406762
Subject(s) - pyridinium , alkyl , iridium , chemistry , catalysis , phosphole , asymmetric hydrogenation , pyridine , aryl , organic chemistry , enantioselective synthesis , noyori asymmetric hydrogenation , combinatorial chemistry
Iridium‐catalyzed asymmetric hydrogenation of N ‐alkyl‐2‐alkylpyridinium salts provided 2‐aryl‐substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral‐phosphole‐based MP 2 ‐SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines.