Construction of α-methoxyimidoyl ketonitrones via phosphite-mediated addition of α-keto N-tert-butanesulfinyl imidates to nitrosoarenes

Chemical Communications : Chem Comm
Jie FengChong-Dao Lu

Abstract

A dimethyl phosphite-mediated addition of α-keto N-tert-butanesulfinyl imidates to nitrosoarenes was developed. Nitrosoarenes were successfully used as electrophiles to trap aza-enolate intermediates that were generated from nucleophilic addition of deprotonated phosphite to α-keto N-tert-butanesulfinyl imidates and following phospha-Brook rearrangement, allowing efficient construction of ketonitrones with excellent (Z)-geometries.

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Citations

Nov 27, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Francisco Foubelo, Miguel Yus
Nov 15, 2020·Chemical Communications : Chem Comm·Anisha PurkaitChandan K Jana

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Methods Mentioned

BETA
X-ray
NMR

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