Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: A facile one-pot procedure

Hoi Lun Kwong; Di Liu; Ka Yee Chan; Chi Sing Lee; Ka Hung Huang; Chi Ming Che

doi:10.1016/j.tetlet.2004.03.107

Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)₂: A facile one-pot procedure

Hoi Lun Kwong^*
, Di Liu
, Ka Yee Chan
, Chi Sing Lee
, Ka Hung Huang
, Chi Ming Che^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

62 Citations (Scopus)

Abstract

A facile one-pot procedure for copper-catalyzed PhI(OAc) ₂-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)₂ and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol% of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination.

Original language	English
Pages (from-to)	3965-3968
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2004.03.107
Publication status	Published - 10 May 2004

User-Defined Keywords

One-pot asymmetric aziridination
Copper catalyst
Styrene
Iodobenzene diacetate
Sulfonamides

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10.1016/j.tetlet.2004.03.107

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@article{371e097c7cdc44fb9b962e5eb952b8d1,

title = "Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: A facile one-pot procedure",

abstract = "A facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol\% of the chiral copper catalyst, these conditions afforded 94\% yield of the isolated product with 75\% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination.",

keywords = "One-pot asymmetric aziridination, Copper catalyst, Styrene, Iodobenzene diacetate, Sulfonamides",

author = "Kwong, \{Hoi Lun\} and Di Liu and Chan, \{Ka Yee\} and Lee, \{Chi Sing\} and Huang, \{Ka Hung\} and Che, \{Chi Ming\}",

note = "Publisher Copyright: {\textcopyright} 2004 Elsevier Ltd. All rights reserved. Funding Information: Financial support for this research project from the Hong Kong Research Grants Council CERG grant (CityU 1119/00P), the Area of Excellence Scheme established under the University Grants Committee of the Hong Kong SAR, China (Project No AoE/P-10/01), and the City University of Hong Kong are gratefully acknowledged.",

year = "2004",

month = may,

day = "10",

doi = "10.1016/j.tetlet.2004.03.107",

language = "English",

volume = "45",

pages = "3965--3968",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2

T2 - A facile one-pot procedure

AU - Kwong, Hoi Lun

AU - Liu, Di

AU - Chan, Ka Yee

AU - Lee, Chi Sing

AU - Huang, Ka Hung

AU - Che, Chi Ming

N1 - Publisher Copyright: © 2004 Elsevier Ltd. All rights reserved. Funding Information: Financial support for this research project from the Hong Kong Research Grants Council CERG grant (CityU 1119/00P), the Area of Excellence Scheme established under the University Grants Committee of the Hong Kong SAR, China (Project No AoE/P-10/01), and the City University of Hong Kong are gratefully acknowledged.

PY - 2004/5/10

Y1 - 2004/5/10

N2 - A facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol% of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination.

AB - A facile one-pot procedure for copper-catalyzed PhI(OAc) 2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhI=NR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5mol% of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination.

KW - One-pot asymmetric aziridination

KW - Copper catalyst

KW - Styrene

KW - Iodobenzene diacetate

KW - Sulfonamides

UR - https://www.scopus.com/pages/publications/1942504284

U2 - 10.1016/j.tetlet.2004.03.107

DO - 10.1016/j.tetlet.2004.03.107

M3 - Journal article

AN - SCOPUS:1942504284

SN - 0040-4039

VL - 45

SP - 3965

EP - 3968

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)₂: A facile one-pot procedure

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