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Asymmetric Allylic Alkylation of β‐Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst
Author(s) -
Kita Yusuke,
Kavthe Rahul D.,
Oda Hiroaki,
Mashima Kazushi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508757
Subject(s) - allylic rearrangement , tsuji–trost reaction , catalysis , chemistry , enantioselective synthesis , yield (engineering) , alkylation , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
Abstract Asymmetric allylic alkylation of β‐ketoesters with allylic alcohols catalyzed by [Ni(cod) 2 ]/( S )‐H 8 ‐BINAP was found to be a superior synthetic protocol for constructing quaternary chiral centers at the α‐position of β‐ketoesters. The reaction proceeded in high yield and with high enantioselectivity using various β‐ketoesters and allylic alcohols, without any additional activators. The versatility of this methodology for accessing useful and enantioenriched products was demonstrated.