Amberlyst-15-catalyzed intramolecular S(N)2 ' oxaspirocyclization of tertiary allylic alcohols

Authors
Young, JJ Jung, LJ Cheng, KM
Citation
Jj. Young et al., Amberlyst-15-catalyzed intramolecular S(N)2 ' oxaspirocyclization of tertiary allylic alcohols, TETRAHEDR L, 41(18), 2000, pp. 3411-3413
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
18
Year of publication
2000
Pages
3411 - 3413
Database
ISI
SICI code
0040-4039(20000429)41:18<3411:AIS'OO>2.0.ZU;2-2
Abstract
A variety of substituted 1-oxaspiro[4,5]dec-6-ene and 1-oxaspiro[5,5]undec- 7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed S(N)2' oxaspirocyclizations under mild reaction conditions (-20 degrees C) in qua ntitative yields. In this process, a tertiary allylic alcohol serves as the precursor of pi-allylic carbocation and the primary, secondary or tertiary alcohol within the same molecule serves as the nucleophile, (C) 2000 Elsev ier Science Ltd. All rights reserved.