N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines

Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl3 mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydrox...

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Main Authors:	Jaipal R. Nagireddy, Geoffrey K. Tranmer, Emily Carlson, William Tam
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	azabicycloalkene β-hydroxyketone 2-isoxazoline oxabicycloalkene Raney nickel
Online Access:	https://doi.org/10.3762/bjoc.10.227

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spelling	doaj-e3ea537abe0043258536b734186d38bc2021-02-02T08:46:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-09-011012200220510.3762/bjoc.10.2271860-5397-10-227N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolinesJaipal R. Nagireddy0Geoffrey K. Tranmer1Emily Carlson2William Tam3Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, CanadaGuelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, CanadaGuelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, CanadaGuelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, CanadaTransition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl3 mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66–95%) and without the need for chromatographic purification.https://doi.org/10.3762/bjoc.10.227azabicycloalkeneβ-hydroxyketone2-isoxazolineoxabicycloalkeneRaney nickel
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Jaipal R. Nagireddy Geoffrey K. Tranmer Emily Carlson William Tam
spellingShingle	Jaipal R. Nagireddy Geoffrey K. Tranmer Emily Carlson William Tam N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines Beilstein Journal of Organic Chemistry azabicycloalkene β-hydroxyketone 2-isoxazoline oxabicycloalkene Raney nickel
author_facet	Jaipal R. Nagireddy Geoffrey K. Tranmer Emily Carlson William Tam
author_sort	Jaipal R. Nagireddy
title	N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_short	N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_full	N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_fullStr	N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_full_unstemmed	N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_sort	n–o cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2014-09-01
description	Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl3 mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66–95%) and without the need for chromatographic purification.
topic	azabicycloalkene β-hydroxyketone 2-isoxazoline oxabicycloalkene Raney nickel
url	https://doi.org/10.3762/bjoc.10.227
work_keys_str_mv	AT jaipalrnagireddy nocleavagereactionsofheterobicycloalkenefused2isoxazolines AT geoffreyktranmer nocleavagereactionsofheterobicycloalkenefused2isoxazolines AT emilycarlson nocleavagereactionsofheterobicycloalkenefused2isoxazolines AT williamtam nocleavagereactionsofheterobicycloalkenefused2isoxazolines
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N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines

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