Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3 + 2] annulation of the Morita–Baylis–Hillman carbonates with pyrazoloneyldiene oxindoles

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Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3 + 2] annulation of the Morita–Baylis–Hillman carbonates with pyrazoloneyldiene oxindoles†

Jing Zhang,

^ab Wai-Lun Chan,

^b Ligong Chen,

^a Nisar Ullah*^c and Yixin Lu

*^bd

Author affiliations

* Corresponding authors

^a School of Chemical Engineering and Technology, Tianjin University, Tianjin, China

^b Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
E-mail: chmlyx@nus.edu.sg

^c Chemistry Department, King Fahd University of Petroleum and Materials, Dhahran 31261, Saudi Arabia
E-mail: nullah@kfupm.edu.sa

^d National University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Suzhou, China

Abstract

A [3 + 2] annulation between the Morita–Baylis–Hillman (MBH) carbonates and pyrazoloneyldiene oxindoles catalyzed by (S)-SITCP has been developed. Structurally novel bispiro[pyrazolone-3,3′-oxindoles] containing two contiguous quaternary stereogenic centers were created in excellent yields, in a diastereospecific and highly enantioselective manner.

This article is part of the themed collection: 2019 Organic Chemistry Frontiers HOT articles

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Article information

DOI: https://doi.org/10.1039/C9QO00471H
Article type: Research Article
Submitted: 03 Apr 2019
Accepted: 01 May 2019
First published: 06 May 2019

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Org. Chem. Front., 2019,6, 2210-2214

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