1,3-DIPOLAR CYCLOADDITIONS TO 5-METHOXY-2(5H)-FURANONE

Authors
KELLER E DELANGE B RISPENS MT FERINGA BL
Citation
E. Keller et al., 1,3-DIPOLAR CYCLOADDITIONS TO 5-METHOXY-2(5H)-FURANONE, Tetrahedron, 49(39), 1993, pp. 8899-8910
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
39
Year of publication
1993
Pages
8899 - 8910
Database
ISI
SICI code
0040-4020(1993)49:39<8899:1CT5>2.0.ZU;2-H
Abstract
Various nitrile oxides and nitrones, ethyl diazoacetate and an azometh ine ylide were examined in 1,3-dipolar cycloadditions to 5-methoxy-2[5 H]-furanone, in particular with respect to regio- and diastereoselecti vities. Isoxazoles 13-17 and isoxazolidines 21, 22 and 24 were obtaine d in high yields with and-facial selectivities and regioselectivities exceeding 95%. In the case of pyrazoline 26 minor amounts of syn-facia l adduct are also observed, whereas lactone annulated pyrrolidines 28 are obtained as mixtures of regio-isomers.