Issue 22, 2016
From the journal:

RSC Advances

Formal [3 + 3] annulation of isatin-derived 2-bromoenals with 1,3-dicarbonyl compounds enabled by Lewis acid/N-heterocyclic carbene cooperative catalysis†

Junyu Xu,‡a   Weiguo Zhang,‡a   Yishan Liu,a   Suzhen Zhu,a   Ming Liu,a   Xi Hua,a   Siyi Chen,a   Tao Lu*a  and  Ding Du*a  

* Corresponding authors

a State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing, P. R. China
E-mail: lut163@163.com, ddmn9999@cpu.edu.cn

Abstract

A series of novel isatin-derived 2-bromoenals were synthesized and applied in a formal [3 + 3] annulation with 1,3-dicarbonyl compounds enabled by a NHC/Lewis acid cooperative catalysis strategy. This newly developed methodology offers rapid access to functionalized spirooxindole δ-lactones. The newly synthesized isatin-derived 2-bromoenals may be further used as potential electrophilic 1,3-synthons for the diversity-oriented synthesis of spirooxindoles.

Graphical abstract: Formal [3 + 3] annulation of isatin-derived 2-bromoenals with 1,3-dicarbonyl compounds enabled by Lewis acid/N-heterocyclic carbene cooperative catalysis

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Article information

DOI
https://doi.org/10.1039/C5RA27848A
Article type
Communication
Submitted
06 Jan 2016
Accepted
27 Jan 2016
First published
29 Jan 2016

RSC Adv., 2016,6, 18601-18606

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Formal [3 + 3] annulation of isatin-derived 2-bromoenals with 1,3-dicarbonyl compounds enabled by Lewis acid/N-heterocyclic carbene cooperative catalysis

J. Xu, W. Zhang, Y. Liu, S. Zhu, M. Liu, X. Hua, S. Chen, T. Lu and D. Du, RSC Adv., 2016, 6, 18601 DOI: 10.1039/C5RA27848A

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