Issue 6, 2017
From the journal:

Organic Chemistry Frontiers

Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities†

Jing Li,‡ab   Zequan Li,‡ab   Xun Zhang,‡ab   Bing Xuab  and  Yian Shi*acd  

* Corresponding authors

a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

b University of Chinese Academy of Sciences, Beijing 100049, P. R. China

c State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Center for Multimolecular Organic Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

d Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA
E-mail: Yian.Shi@colostate.edu

Abstract

A highly enantioselective bromohydroxylation of aryl olefins with flexible functionalities has been achieved with (DHQD)2PHAL as a catalyst and H2O as a nucleophile, giving a variety of optically active bromohydrins with up to 98% ee. An acid additive has been found to be beneficial for the reactivity and enantioselectivity.

Graphical abstract: Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities

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Article information

DOI
https://doi.org/10.1039/C6QO00636A
Article type
Research Article
Submitted
18 Oct 2016
Accepted
21 Feb 2017
First published
22 Feb 2017

Org. Chem. Front., 2017,4, 1084-1090

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Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities

J. Li, Z. Li, X. Zhang, B. Xu and Y. Shi, Org. Chem. Front., 2017, 4, 1084 DOI: 10.1039/C6QO00636A

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