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. 2011 Apr 15;13(8):1924-7.
doi: 10.1021/ol2002418. Epub 2011 Mar 25.

Allene functionalization via bicyclic methylene aziridines

Luke A Boralsky  1 , Dagmara Marston, R David Grigg, John C Hershberger, Jennifer M Schomaker
Affiliations

Allene functionalization via bicyclic methylene aziridines

Luke A Boralsky et al. Org Lett. .

Abstract

The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. This paper describes the use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons.

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Figures

Scheme 1
Scheme 1
Proposed allene functionalization.
Scheme 2
Scheme 2
Nucleophilic ring opening of bicyclic MAs.
See this image and copyright information in PMC

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