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Issue 16, 2013
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An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

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Abstract

The first organocatalytic Michael–cyclization cascade reaction between isothiocyanato oxindoles and unsaturated pyrazolones has been developed. The multicyclic spiro[oxindole/thiobutyrolactam/pyrazolone] core structures containing three contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent diastereo- (up to >20 : 1) and enantioselectivities (up to 99% ee).

Graphical abstract: An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

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Article information


Submitted
21 Nov 2012
Accepted
07 Jan 2013
First published
08 Jan 2013

Chem. Commun., 2013,49, 1657-1659
Article type
Communication

An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

Q. Chen, J. Liang, S. Wang, D. Wang and R. Wang, Chem. Commun., 2013, 49, 1657
DOI: 10.1039/C3CC38386E

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