UNPRECEDENTED REARRANGEMENT OF 5-BENZOYL SUBSTITUTED BICYCLIC ISOXAZOLIDINES TO DEHYDRO PYRROLIZIDIN-2-ONES AND INDOLIZIDIN-2-ONES

Authors
CORDERO FM BRANDI A DESARLO F VITI G
Citation
Fm. Cordero et al., UNPRECEDENTED REARRANGEMENT OF 5-BENZOYL SUBSTITUTED BICYCLIC ISOXAZOLIDINES TO DEHYDRO PYRROLIZIDIN-2-ONES AND INDOLIZIDIN-2-ONES, Journal of the Chemical Society, Chemical Communications, (9), 1994, pp. 1047-1048
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
9
Year of publication
1994
Pages
1047 - 1048
Database
ISI
SICI code
0022-4936(1994):9<1047:URO5SB>2.0.ZU;2-X
Abstract
5-Benzoyl substituted isoxazolidines 3, obtained by 1,3-dipolar cycloa dditions of pyrroline N-oxide and tetrahydropyridine N-oxide to phenyl vinyl ketone, undergo a rearrangement to dehydro 3-phenyl-pyrrolizidi n-2-one and 3-phenylindolizidin-2-one catalysed by Al2O3; the rearrang ement products undergo a Michael addition to a second molecule of phen yl vinyl ketone.