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

ABSTRACT: 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.

SUBMITTER: Brichacek M

PROVIDER: S-EPMC2646081 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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

Brichacek Matthew M Lee Dongeun D Njardarson Jon T JT

Organic letters 20081009 21

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. ...[more]

PMID: 18841992

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