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Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones

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Abstract

A tertiary amine catalyzed highly diastereoselective and enantioselective [3 + 2] annulation between Morita–Baylis–Hillman (MBH) carbonates derived from isatin and pyrazolone 4,5-diones has been developed. A series of structurally diverse and multifunctional spirooxindole dihydrofuran fused pyrazolone derivatives with two adjacent quaternary spirocenters has been achieved in excellent yields with good to excellent enantioselectivity. Further synthetic utility of this protocol has been successfully demonstrated by employing the bromo derivative of spirooxindole dihydrofuran fused pyrazolone to Suzuki coupling.

Graphical abstract: Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones

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Article information


Submitted
02 Jan 2020
Accepted
07 Feb 2020
First published
11 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones

P. K. Warghude, A. S. Sabale and R. G. Bhat, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00007H

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