Kinetic resolution of racemic 2-substituted 1, 2-dihydroquinolines via asymmetric Cu-catalyzed borylation. Issue 6 (4th May 2017)

• Record Type: Journal Article
• Authors: Kong, Duanyang; Han, Suna; Wang, Rui; Li, Meina; Zi, Guofu; Hou, Guohua
• Is Part Of: Chemical science. Volume 8:Issue 6(2017)
• Page Start: 4558
• Page End: 4564
• Publication Date: 2017-05-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc01556a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A highly efficient kinetic resolution of racemic 2-substituted 1, 2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been realized for the first time to afford chiral 3-boryl-1, 2, 3, 4-tetrahydroquinolines and recover 2-substituted 1, 2-dihydroquinolines with excellent enantioselectivities and selectivity factors of up to 569. Abstract : A highly efficient kinetic resolution of racemic 2-substituted 1, 2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been realized for the first time. Under mild conditions, a variety of chiral 3-boryl-1, 2, 3, 4-tetrahydroquinolines containing two vicinal stereogenic centers as well as the recovered 2-substituted 1, 2-dihydroquinolines were afforded after 30 minutes in high yields with up to 99% ee (dr > 99 : 1) and over 98% ee values, respectively, corresponding to kinetic selectivity factors of up to 569. Moreover, this protocol was successfully applied to the asymmetric synthesis of a selective estrogen receptor modulator.