Asymmetric direct α-alkylation of 2-oxindoles with Michler's hydrol catalyzed by bis-cinchona alkaloid–Brønsted acid via an SN1-type pathway

Tao Zhang; Zhen Qiao; Yan Wang; Nengjun Zhong; Li Liu; Dong Wang; Yong-Jun Chen

doi:10.1039/C3CC39012H

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Asymmetric direct α-alkylation of 2-oxindoles with Michler's hydrol catalyzed by bis-cinchona alkaloid–Brønsted acid via an S_N1-type pathway†

Tao Zhang,^ab Zhen Qiao,^ab Yan Wang,^ab Nengjun Zhong,^ab Li Liu,*^a Dong Wang^a and Yong-Jun Chen^a

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* Corresponding authors

^a Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: lliu@iccas.ac.cn
Fax: +86 10 6255 4449
Tel: +86 10 6255 4614

^b Graduate School of Chinese Academy of Sciences, Beijing 100049, China

Abstract

An enantioselective direct α-alkylation of 2-oxindoles with Michler's hydrol via an S_N1-type pathway in the non-covalent activation mode using the bis-cinchona alkaloid and Brønsted acid as a co-catalyst was developed and good to high yields and enantioselectivities were obtained.

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Article information

DOI: https://doi.org/10.1039/C3CC39012H
Article type: Communication
Submitted: 19 Oct 2012
Accepted: 08 Jan 2013
First published: 09 Jan 2013

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Chem. Commun., 2013,49, 1636-1638

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Asymmetric direct α-alkylation of 2-oxindoles with Michler's hydrol catalyzed by bis-cinchona alkaloid–Brønsted acid via an S_N1-type pathway

T. Zhang, Z. Qiao, Y. Wang, N. Zhong, L. Liu, D. Wang and Y. Chen, Chem. Commun., 2013, 49, 1636 DOI: 10.1039/C3CC39012H

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