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Synfacts 2010(11): 1226-1226
DOI: 10.1055/s-0030-1258761
DOI: 10.1055/s-0030-1258761
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2-Isoxazolines via Conjugate Additions
A. Pohjakallio, P. M. Pihko*, U. M. Laitinen
University of Jyväskylä and Aalto University of Science and Technology, Espoo, Finland
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
Significance
The work reported here describes the development of methodology for the synthesis of 2-isoxazolines via the conjugate addition of oximes to unsaturated aldehydes under acid catalysis, firstly in a racemic manner and this is then extended to an enantioselective process. For the racemic pathway the paper reports extensive screens of the oxime nucleophile as well as catalyst screening to give the final optimized conditions. The enantioselective variant was developed via careful optimization of the employed acid.