X=Y-ZH Systems as potential 1,3-dipoles. Part 52: Fused-ring forming electrophile induced oxime -> nitrone -> cycloaddition cascades

Authors
Dondas, HA Grigg, R Thibault, S
Citation
Ha. Dondas et al., X=Y-ZH Systems as potential 1,3-dipoles. Part 52: Fused-ring forming electrophile induced oxime -> nitrone -> cycloaddition cascades, TETRAHEDRON, 57(32), 2001, pp. 7035-7045
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
32
Year of publication
2001
Pages
7035 - 7045
Database
ISI
SICI code
0040-4020(20010806)57:32<7035:XSAP1P>2.0.ZU;2-K
Abstract
Electrophile induced cyclisation of oximes onto endocyclic alkenes and exo- methylene cycloalkanes occurs stereo- and regiospecifically generating cis- fused bicyclic nitrones in good yield. Subsequent facially selective cycloa ddition with N-methylmaleimide occurs in good yield. The sequence may be ca rried out as a one-pot procedure and results in the formation of 4 bonds, 2 rings and 6 stereocentres. (C) 2001 Elsevier Science Ltd. All rights reser ved.