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Nickel‐Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes
Author(s) -
Jin Youxiang,
Wang Chuan
Publication year - 2019
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.201901067
Subject(s) - stereocenter , nickel , chemistry , catalysis , aryl , intramolecular force , alkyl , reductive elimination , cascade , combinatorial chemistry , benzene , cascade reaction , medicinal chemistry , enantioselective synthesis , organic chemistry , chromatography
Reported is an asymmetric reductive dicarbofunctionalization of unactivated alkenes. Under the catalysis of a Ni/BOX system, various aryl bromides, incorporating a pendant olefinic unit, were successfully reacted with an array of primary alkyl bromides in the presence of Zn as a reductant, furnishing a series of benzene‐fused cyclic compounds bearing a quaternary stereocenter in high enantioselectivities. Notably, this reaction avoids the use of pregenerated organometallics and demonstrates high tolerance of sensitive functionalities. The preliminary mechanistic investigations reveal that this Ni‐catalyzed reaction proceeds as a cascade consisting of migratory insertion and cross‐coupling with a nickel(I)‐mediated intramolecular 5‐ exo cyclization as the enantiodetermining step.