Issue 11, 2016
From the journal:

Chemical Communications

An asymmetric assembly of spirooxindole dihydropyranones through a direct enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins†

Jeng-Liang Han*a  and  Chia-Hao Changa  

* Corresponding authors

a Department of Chemistry, Chung Yuan Christian University, Taoyuan City, Taiwan 32023
E-mail: jlhan@cycu.edu.tw

Abstract

A highly enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles to isatins has been achieved by using bifunctional organocatalysts. The unexpected intramolecular lactonization which follows the initial aldol reaction, leading to the cleavage of the oxindole ring and generation of enantioenriched spirooxindole dihydropyranones in good to excellent yields with high enantioselectivities.

Graphical abstract: An asymmetric assembly of spirooxindole dihydropyranones through a direct enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins

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Article information

DOI
https://doi.org/10.1039/C5CC08883F
Article type
Communication
Submitted
26 Oct 2015
Accepted
15 Dec 2015
First published
15 Dec 2015

Chem. Commun., 2016,52, 2322-2325

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An asymmetric assembly of spirooxindole dihydropyranones through a direct enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins

J. Han and C. Chang, Chem. Commun., 2016, 52, 2322 DOI: 10.1039/C5CC08883F

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