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Issue 6, 2017
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Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation

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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

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Article information


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

Chem. Sci., 2017,8, 4558-4564
Article type
Edge Article

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

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