Issue 10, 2014
From the journal:

Chemical Communications

Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade†

Long Han,ab   Chuan Liu,b   Wei Zhang,*b   Xiao-Xin Shia  and  Shu-Li You*ab  

* Corresponding authors

a School of Pharmacy, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, China

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
E-mail: zhangwei@sioc.ac.cn, slyou@sioc.ac.cn
Fax: +86 21-54925087

Abstract

An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.

Graphical abstract: Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade

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Article information

DOI
https://doi.org/10.1039/C3CC47921H
Article type
Communication
Submitted
15 Oct 2013
Accepted
24 Nov 2013
First published
26 Nov 2013

Chem. Commun., 2014,50, 1231-1233

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Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade

L. Han, C. Liu, W. Zhang, X. Shi and S. You, Chem. Commun., 2014, 50, 1231 DOI: 10.1039/C3CC47921H

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