Issue 6, 2017

Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

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.

Graphical abstract: Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Feb 2017
Accepted
11 Apr 2017
First published
19 Apr 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 4558-4564

Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

D. Kong, S. Han, R. Wang, M. Li, G. Zi and G. Hou, Chem. Sci., 2017, 8, 4558 DOI: 10.1039/C7SC01556A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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