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Synthesis 2014; 46(04): 503-509
DOI: 10.1055/s-0033-1340464
DOI: 10.1055/s-0033-1340464
paper
One-Pot Synthesis of Isoxazolines from Aldehydes Catalyzed by Iodobenzene
Further Information
Publication History
Received: 24 October 2013
Accepted after revision: 25 November 2013
Publication Date:
12 December 2013 (online)
Abstract
A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.
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