Copper‐Catalyzed Enantioselective Hydroboration of 1, 1‐Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies. Issue 1 (13th November 2017)

• Record Type: Journal Article
• Authors: Wen, Lu; Cheng, Fengchang; Li, Han; Zhang, Shuoqing; Hong, Xin; Meng, Fanke
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 1(2018)
• Page Start: 103
• Page End: 106
• Publication Date: 2017-11-13
• Subjects: asymmetric catalysis -- copper -- copper–boron addition -- hydroboration -- organoboron compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700503
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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. Abstract : Copper statues : Copper‐catalyzed enantioselective formation of tertiary alkyl‐copper complexes followed by protonation affords hydroboration products in high yields and with excellent enantioselectivity.