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Highly Regio- and Diastereoselective [3+2]-Cycloadditions Involving Indolediones and α,β-Disubstituted Nitroethylenes

Abstract

A highly diastereoselective [3+2]-cycloaddition strategy between multiple oxindoles and several α,β-disubstituted nitroethylenes is developed to access tetra substituted α-spiropyrrolidine frameworks. Variety of α-aminoacids were employed for the first time in order to generate azomethine ylides under thermal conditions affording regioisomers 13 and 14 by mere change of α-substituent (R=H and substituted carbon) in α-aminoacids. The reaction tolerates various sterically demanding, electron-rich and electron-deficient aryl and nitrogen substituents on glycines, oxindoles and nitroethylenes. The operational simplicity, such as the use of metal and inert-free atmosphere, utility of non-halogenated solvent and easy isolation - the principles of green chemistry, is attractive for scale up opportunities. The reaction delivers good yields (80-94%), diastereoselectivities (up to 98:2) in the favor of (cis,cis)-spirooxindoles with opposite regioselectivity compared to β-nitrostyrenes, under identical conditions. Two spiropyrrolidine cycloadducts with unprotected amide exhibited significant activity against Gram-positive MRSA.

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Publication details

The article was received on 25 Jun 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01429B
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Highly Regio- and Diastereoselective [3+2]-Cycloadditions Involving Indolediones and α,β-Disubstituted Nitroethylenes

    M. P. Rao, S. S. Gunaga, J. Zuegg, R. Pamarthi and M. Ganesh, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB01429B

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