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Highly Enantioselective Nickel‐Catalyzed Intramolecular Reductive Cyclization of Alkynones
Author(s) -
Fu Wenzhen,
Nie Ming,
Wang Aizhen,
Cao Ziping,
Tang Wenjun
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410700
Subject(s) - enantioselective synthesis , chemistry , intramolecular force , nickel , triethylsilane , allylic rearrangement , reagent , furan , combinatorial chemistry , substrate (aquarium) , pyran , catalysis , ligand (biochemistry) , organic chemistry , oceanography , receptor , geology , biochemistry
The first asymmetric nickel‐catalyzed intramolecular reductive cyclization of alkynones is reported. A P‐chiral monophosphine and triethylsilane were used as the ligand and the reducing reagent, respectively, to form a series of tertiary allylic alcohols bearing furan/pyran rings in excellent yields and enantioselectivities. This reaction has a broad substrate scope and enabled the efficient synthesis of dehydroxycubebin and chiral dibenzocyclooctadiene skeletons.