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Iridium‐Catalyzed Asymmetric Hydrogenation of Unfunctionalized Exocyclic C=C Bonds
Author(s) -
Xia Jingzhao,
Yang Guoqiang,
Zhuge Ruijing,
Liu Yangang,
Zhang Wanbin
Publication year - 2016
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.201604298
Subject(s) - asymmetric hydrogenation , chemistry , iridium , oxazoline , catalysis , indene , enantioselective synthesis , phosphine , organic chemistry , double bond , noyori asymmetric hydrogenation , enantiomeric excess , medicinal chemistry , enantiomer
Abstract An iridium‐catalyzed asymmetric hydrogenation of unfunctionalized exocyclic C=C bonds was performed by using an axially flexible chiral phosphine–oxazoline ligand, providing the desired chiral 1‐benzyl‐2,3‐dihydro‐1 H ‐indene products with up to 98 % ee (enantiomeric excess). This represents the first general hydrogenation of unfunctionalized exocyclic olefins with high selectivity reported thus far. The additive acetate ion plays an important role in the reaction's high enantioselectivity. The chiral product can be further transformed into key intermediates required for the synthesis of an important insecticide and a drug compound.