Palladium-catalyzed [2+2] cycloaddition of allylic acetates and norbornene

Authors
Tsukada, N Sato, T Inoue, Y
Citation
N. Tsukada et al., Palladium-catalyzed [2+2] cycloaddition of allylic acetates and norbornene, TETRAHEDR L, 41(21), 2000, pp. 4181-4184
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
21
Year of publication
2000
Pages
4181 - 4184
Database
ISI
SICI code
0040-4039(20000529)41:21<4181:P[COAA>2.0.ZU;2-0
Abstract
Palladium-catalyzed reaction of norbornene with allyl acetate gave 3-methyl enetricyclo[4.2.1.0(2,5)]nonane 1 and 2-methylene-3-vinylnorbornane 2 in hi gh yields. The substituents on allyl acetate strongly influenced the select ivity. In the reactions of 1- or 3-substituted allyl acetates, cycloadducts corresponding to 1 were obtained exclusively. Use of methallyl acetate gav e solely a diene corresponding to 2. (C) 2000 Elsevier Science Ltd. All rig hts reserved.