Copper‐Catalyzed Enantioselective Hydroboration of 1,1‐Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies | Zendy

Wen Lu | Zendy; Cheng Fengchang | Zendy; Li Han | Zendy; Zhang Shuoqing | Zendy; Hong Xin | Zendy; Meng Fanke | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research