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

doi:10.1081/SCC-120030324

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

Research output: Contribution to journal › Article › peer-review

26 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 language	English (US)
Pages (from-to)	1337-1347
Number of pages	11
Journal	Synthetic Communications
Volume	34
Issue number	7
DOIs	https://doi.org/10.1081/SCC-120030324
State	Published - 2004
Externally published	Yes

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

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.",

keywords = "Alkenes, Aziridination, N-Arylsulfonyl aziridine, P-Toluenesulfonamide",

author = "Nadir, {Upender K.} and Anamika Singh",

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.",

year = "2004",

doi = "10.1081/SCC-120030324",

language = "English (US)",

volume = "34",

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T1 - Synthesis of Functionalized N-Arylsulfonyl Aziridines from α,β-Unsaturated Esters, Amides, Ketones, and Nitriles Using N,N-Dichloroarylsulfonamides as Nitrogen Source

AU - Nadir, Upender K.

AU - Singh, Anamika

N1 - 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.

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - Alkenes

KW - Aziridination

KW - N-Arylsulfonyl aziridine

KW - P-Toluenesulfonamide

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VL - 34

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JO - Synthetic Communications

JF - Synthetic Communications

IS - 7

ER -

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

Abstract

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Keywords

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