The diastereoselective synthesis of functionalised isoxazolidines using a Cope elimination/intramolecular nitrone cycloaddition strategy

Authors :: O'Neil, Ian A.
Ramos, V. Elena
Ellis, Gemma L.
Cleator, Ed
Chorlton, Alan P.
Tapolczay, David J.
Kalindjian, S. Barret
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Apr2004, Vol. 45 Issue 18, p3659. 3p.
Publication Year :: 2004
Abstract: Functionalised hydroxylamine derivatives of (S)-prolinol prepared by a Cope elimination have been found to undergo oxidation to the nitrone either in the presence of air or a catalytic quantity of TPAP. These undergo intramolecular cycloaddition to give tricyclic isoxazolidines with high diastereoselectivity. [Copyright &y& Elsevier]

Subjects :: *HYDROXYLAMINE
*RING formation (Chemistry)
*OXIDATION
*CHEMICAL reactions

Language :: English
ISSN :: 00404039
Volume :: 45
Issue :: 18
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 12776131
Full Text :: https://doi.org/10.1016/j.tetlet.2004.03.041

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