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Copper‐Catalyzed Enantioselective Hydroboration of 1,1‐Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies
Author(s) -
Wen Lu,
Cheng Fengchang,
Li Han,
Zhang Shuoqing,
Hong Xin,
Meng Fanke
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700503
Subject(s) - enantioselective synthesis , hydroboration , chemistry , stereocenter , moiety , stereochemistry , enantiomer , protonation , borane , organic chemistry , catalysis , combinatorial chemistry , ion
Cu‐catalyzed enantioselective Cu–B(pin) addition to 1,1‐disubstituted alkenes generating tertiary alkylcopper complexes that contain a quaternary stereogenic center, followed by the protonation of the complexes are presented. The resulting formal hydroboration products are formed in up to 98 % yield and 99:1 enantiomeric ratio. The C–B(pin) moiety can be converted to a variety of useful functional groups. The method is applied to the enantioselective formal synthesis of ( R )‐ketoprofen. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations.