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Issue 3, 2020
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A new tandem synthesis of bis(β,β′-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions

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Abstract

An efficient and new approach has been developed to synthesize bis(β,β′-dialkoxy carbonyl) derivatives through the reaction between N-tosylaziridines and malonate esters under ambient air using tBuOK in DMSO solvent. A plausible reaction pathway has been predicted. Control experiments suggested that the reactions proceed through the formation of α-aminoketones. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and simple operation. A gram-scale synthesis demonstrates the potential applications of the present method.

Graphical abstract: A new tandem synthesis of bis(β,β′-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions

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Article information


Submitted
13 Nov 2019
Accepted
16 Dec 2019
First published
16 Dec 2019

Org. Biomol. Chem., 2020,18, 551-556
Article type
Paper

A new tandem synthesis of bis(β,β′-dialkoxy carbonyl) compounds by oxidative cleavage of aziridines under metal-free conditions

S. Samanta, S. Santra, R. Chatterjee and A. Majee, Org. Biomol. Chem., 2020, 18, 551
DOI: 10.1039/C9OB02451D

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