Reaction of vinylcarbenoids with aldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans

Authors
Hamaguchi, M Matsubara, H Nagai, T
Citation
M. Hamaguchi et al., Reaction of vinylcarbenoids with aldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans, TETRAHEDR L, 41(9), 2000, pp. 1457-1460
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
9
Year of publication
2000
Pages
1457 - 1460
Database
ISI
SICI code
0040-4039(20000226)41:9<1457:ROVWAF>2.0.ZU;2-N
Abstract
Rh-2(OAc)(4)-catalyzed reaction of vinyldiazo compound 1 in the presence of benzaldehydes 2a-2c gave a mixture of isomeric vinyloxiranes 3 and 4, and sterically unstable (E)-dihydrofurans 5, but not stable (Z)-dihydrofurans 6 . However, the reaction in the presence of maleic anhydride gave single 1,3 -dipolar cycloadducts 15, indicating that onyl endo-aryl-endo-cyanostyryl c arbonyl ylide 7 (8) is initially formed in the reaction of 1 with 2. (C) 20 00 Elsevier Science Ltd. All rights reserved.