Diastereoselective tandem oxidation/Michael/aldol reaction: unprecedented formation of dispirocyclopentanebisoxindoles and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′diones

Koorathota Suman; Mala Ramanjaneyulu; Sathiah Thennarasu

doi:10.1039/C6OB02607A

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Diastereoselective tandem oxidation/Michael/aldol reaction: unprecedented formation of dispirocyclopentanebisoxindoles and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′diones†

Koorathota Suman,^a Mala Ramanjaneyulu^ab and Sathiah Thennarasu

*^ab

Author affiliations

* Corresponding authors

^a Organic and Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai, Tamilnadu, India-600020
E-mail: thennarasu@gmail.com

^b Academy of Scientific and Innovative Research (AcSIR), Anusandhan Bahavan, 2 Rafi Marg, New Delhi-110001, India
Fax: (+) 91-44-24911589

Abstract

An unprecedented tandem oxidation/Michael/aldol reaction is reported. The diastereoselective formation of only a single isomer of dispirocyclopentanebisoxindole and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′dione is presented. The reaction generates two new C–C bonds and two all-carbon quaternary chiral stereocenters in a single step.

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DOI: https://doi.org/10.1039/C6OB02607A
Article type: Communication
Submitted: 29 Nov 2016
Accepted: 02 Feb 2017
First published: 02 Feb 2017

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Org. Biomol. Chem., 2017,15, 1961-1964

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Diastereoselective tandem oxidation/Michael/aldol reaction: unprecedented formation of dispirocyclopentanebisoxindoles and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′diones

K. Suman, M. Ramanjaneyulu and S. Thennarasu, Org. Biomol. Chem., 2017, 15, 1961 DOI: 10.1039/C6OB02607A

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Organic & Biomolecular Chemistry

Diastereoselective tandem oxidation/Michael/aldol reaction: unprecedented formation of dispirocyclopentanebisoxindoles and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′diones†

Abstract

Supplementary files

Article information

Download Citation

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Diastereoselective tandem oxidation/Michael/aldol reaction: unprecedented formation of dispirocyclopentanebisoxindoles and dispiro[acenaphthylene-1,1′-cyclopentane-3′,1′′-acenaphthylene]-2,2′′diones

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