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Synlett 2012; 23(16): 2293-2297
DOI: 10.1055/s-0032-1317096
DOI: 10.1055/s-0032-1317096
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Recent Developments in Nitrone Chemistry: Some Novel Transformations
Further Information
Publication History
Received: 06 July 2012
Accepted after revision: 23 July 2012
Publication Date:
11 September 2012 (online)
Abstract
Despite the long history of nitrone chemistry, novel transformations of nitrones continue to be discovered. This article describes some recent breakthroughs in the development of new transformations of nitrones. These new reactions include formal [3+3] cycloaddition of nitrones and vinylcarbenes to give 3,6-dihydro-1,2-oxazines, tandem cyclization–[3+3] cycloaddition of nitrones and enynones to give furo[3,4-d][1,2]oxazines, [2+2+3] cycloaddition of nitrones and 1,6-enynes to give tricyclic 1,2-oxazepanes, reaction of nitrones and 2-azido acrylates to form 1,2,4,5-tetrasubstituted imidazoles, and reactions of α,β-unsaturated N-aryl ketonitrones and activated alkynes to generate C3-quaternary indolenines.
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For some early reviews:
For the initial report, see:
For examples of catalytic asymmetric versions, see:
The formal [3+3] cycloaddition of nitrones and 1,1-cyclopropane diesters was also designated as homo [3+2] dipolar cycloaddition:
For related Pd-catalyzed formal [3+3] and [4+3] cycloaddition of N,α-diarylnitrones, see:
For some related transformations, see:
For some examples of indolenines in syntheses of indole-containing natural products, see: