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A d ‐Camphor‐Based Schiff Base as a Highly Efficient N,P Ligand for Enantioselective Palladium‐Catalyzed Allylic Substitutions
Author(s) -
Liu QiaoLing,
Chen Weifeng,
Jiang QunYing,
Bai XingFeng,
Li Zhifang,
Xu Zheng,
Xu LiWen
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600084
Subject(s) - allylic rearrangement , chemistry , amination , palladium , enantioselective synthesis , catalysis , tsuji–trost reaction , substitution reaction , ligand (biochemistry) , schiff base , medicinal chemistry , organic chemistry , stereochemistry , biochemistry , receptor
New Schiff bases derived from chiral d ‐ camphor were determined to be effective phosphine ligands for the asymmetric palladium‐catalyzed allylic alkylation of activated methylene compounds, the allylic etherification of alcohols, and the allylic amination of primary amines or secondary amines, in which the corresponding products with various functional groups were achieved in good yields with excellent enantioselectivities (up to >99 % ee ). Remarkably, the palladium catalyst derived from Schiff base L2 afforded the highest level of enantioselectivity reported to date for allylic substitution reactions, including allylic etherification and allylic amination, which revealed the privileged role of d ‐camphor‐derived Schiff bases in palladium‐catalyzed allylic substitution reactions.