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Construction of Quaternary Stereogenic Carbon Centers through Copper‐Catalyzed Enantioselective Allylic Alkylation of Azoles
Author(s) -
Ohmiya Hirohisa,
Zhang Heng,
Shibata Saori,
Harada Ayumi,
Sawamura Masaya
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600619
Subject(s) - stereocenter , enantioselective synthesis , tsuji–trost reaction , allylic rearrangement , regioselectivity , chemistry , carbene , alkylation , catalysis , ring (chemistry) , ligand (biochemistry) , stereochemistry , organic chemistry , biochemistry , receptor
Copper‐catalyzed enantioselective allylic alkylation of azoles with γ,γ‐disubstituted primary allylic phosphates was achieved using a new chiral N‐heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all‐carbon quaternary stereogenic center at the position α to the heteroaromatic ring.