Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines

Matthew Brichacek; Dongeun Lee; Jon T. Njardarson

doi:10.1021/ol802123e

Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines

Matthew Brichacek, Dongeun Lee, Jon T. Njardarson

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

74 Scopus citations

Abstract

(Chemical Equation Presented) This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl-and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)₂ was determined to be superior to all other catalysts tested.

Original language	English (US)
Pages (from-to)	5023-5026
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol802123e
State	Published - 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802123e

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title = "Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines",

abstract = "(Chemical Equation Presented) This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl-and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.",

author = "Matthew Brichacek and Dongeun Lee and Njardarson, {Jon T.}",

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AU - Lee, Dongeun

AU - Njardarson, Jon T.

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Y1 - 2008

N2 - (Chemical Equation Presented) This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl-and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.

AB - (Chemical Equation Presented) This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl-and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.

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M3 - Article

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JO - Organic Letters

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Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines

Abstract

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