Synthesis of Functionalized N-Arylsulfonyl Aziridines from α,β-Unsaturated Esters, Amides, Ketones, and Nitriles Using N,N-Dichloroarylsulfonamides as Nitrogen Source

Upender K. Nadir, Anamika Singh

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22 Scopus citations

Abstract

A convenient and general aziridination process has been developed for the synthesis of functionalized N-arylsulfonylaziridines bearing an alkoxycarbonyl, acyl, cyano, and carboxamide group at C2. The two-step sequence involves addition of N,N-dichloroarylsulfonamide to the appropriate olefin in the presence of Cu(acac)2, treatment of the resultant chlorosulfonamide with Na2SO3, followed by cyclization with NaOH to give the appropriate aziridine in good yields. The reaction is found to be an anti-stereoselective.

Original languageEnglish (US)
Pages (from-to)1337-1347
Number of pages11
JournalSynthetic Communications
Volume34
Issue number7
DOIs
StatePublished - 2004

Bibliographical note

Funding Information:
This work was supported by project funds from Council of Scientific and Industrial research (CSIR), New Delhi (Government of India organization). The financial support provided by CSIR, New Delhi to AS in the form of senior research fellowship is acknowledged.

Keywords

  • Alkenes
  • Aziridination
  • N-Arylsulfonyl aziridine
  • P-Toluenesulfonamide

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