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Regioselective, Asymmetric Formal Hydroamination of Unactivated Internal Alkenes
Author(s) -
Xi Yumeng,
Butcher Trevor W.,
Zhang Jing,
Hartwig John F.
Publication year - 2016
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.201509235
Subject(s) - regioselectivity , hydroamination , chemistry , enantioselective synthesis , selectivity , catalysis , sulfonamide , combinatorial chemistry , organic chemistry
We report the regioselective and enantioselective formal hydroamination of unsymmetrical internal alkenes catalyzed by a copper catalyst ligated by DTBM‐SEGPHOS. The regioselectivity of the reaction is controlled by the electronic effects of ether, ester, and sulfonamide groups in the homoallylic position. The observed selectivity underscores the influence of inductive effects of remote substituents on the selectivity of catalytic processes occurring at hydrocarbyl groups, and the method provides direct access to various 1,3‐aminoalcohol derivatives with high enantioselectivity.