A Sequential Nitro-Michael Addition and Reductive Cyclization Cascade Reaction for Diastereoselective Synthesis of Multifunc-tionalized 3,3'-pyrrolidinyl-spirooxindoles

10 July 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

In this investigation, we elucidated, one-pot two stage efficient synthesis of multifuctionalized spiro[oxindole-3,3′-pyrrolidine]. The methodology proceeds via organocatalyzed nitro-Michael addition reaction between indolylidenecyanoesters and nitroalkanes to formed nitro-Michael adduct which transformed into multifunctionalized 3,3'-pyrrolidinyl-spirooxindoles by metal catalyzed reductive cyclization cascade. DFT investigations were conducted to elucidate the mechanism underlying the preferential reduction of the nitro group, with subsequent attack on the nitrile and ester groups remain inert throughout the reaction process. The approach is operationally simple, easily scalable, exhibits compatibility with readily accessible starting material and catalysts, thereby emphasizing cost effectiveness.

Keywords

Organocatalysis
Heterogeneous catalysis
diastereoselective spiro[oxindole-3
3′-pyrrolidine]
DFT study

Supplementary materials

Title
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Title
A Sequential Nitro-Michael Addition and Reductive Cyclization Cascade Reaction for Diastereoselective Synthesis of Multifunc-tionalized 3,3'-pyrrolidinyl-spirooxindoles
Description
One pot two stage efficient synthesis of multifuctionalized spiro[oxindole-3,3′-pyrrolidine]. DFT investigations were conducted to elucidate the mechanism underlying regioselective cascade ring closure attack on the nitrile.
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