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Highly regio- and diastereoselective [3 + 2]-cycloadditions involving indolediones and α,β-disubstituted nitroethylenes

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Abstract

A highly diastereoselective [3 + 2]-cycloaddition strategy involving multiple oxindoles and several α,β-disubstituted nitroethylenes is developed to access tetra-substituted α-spiropyrrolidine frameworks. A variety of α-amino acids were employed for the first time in order to generate azomethine ylides under thermal conditions, affording regioisomers 13 and 14 merely by changing the α-substituents (R = H and substituted carbons) of the α-amino acids. 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 a metal-free and non-inert environment, the utilization of non-halogenated solvents and the ease of isolation, adhering to the principles of green chemistry, makes this process attractive for scale-up opportunities. The reaction delivers good yields (80–94%) and diastereoselectivities (up to 98 : 2) in favor of (cis,cis)-spirooxindoles, with opposite regioselectivity compared to β-nitrostyrenes under identical conditions. Two spiropyrrolidine cycloadducts with unprotected amides exhibited significant activity against Gram-positive MRSA.

Graphical abstract: Highly regio- and diastereoselective [3 + 2]-cycloadditions involving indolediones and α,β-disubstituted nitroethylenes

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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, Advance Article

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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, Advance Article , DOI: 10.1039/C9OB01429B

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