Nazarov cyclization of 4-cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-onederivatives. Synthesis of spiro[4.5]decane, spiro[4.4]nonane, and their derivatives

Authors
Kuroda, C Koshio, H Koito, A Sumiya, H Murase, A Hirono, Y
Citation
C. Kuroda et al., Nazarov cyclization of 4-cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-onederivatives. Synthesis of spiro[4.5]decane, spiro[4.4]nonane, and their derivatives, TETRAHEDRON, 56(35), 2000, pp. 6441-6455
Citations number
54
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
35
Year of publication
2000
Pages
6441 - 6455
Database
ISI
SICI code
0040-4020(20000825)56:35<6441:NCO4>2.0.ZU;2-E
Abstract
ASpiro[4.5]decane and spiro[4.4]nonane ring systems were synthesized by FeC l3-induced Nazarov cyclization of alpha-(trimethylsilylmethyl)divinyl keton e derivatives. It was found that the double bond position of the product is controlled by the presence/absence of alpha'-substituent, while trimethyls ilyl group is essential to obtain the products in good yields. Spiro[4.4]no nanes having exo-methylene group underwent rearrangement to bicyclo[4.3.0]n onanes. (C) 2000 Elsevier Science Ltd. All rights reserved.