Reaction of homoallylic alcohols with NaIO4/NaHSO3 reagent - synthesis of alkyl substituted tetrahydrofuran derivatives

Authors
Okimoto, Y Kikuchi, D Sakaguchi, S Ishii, Y
Citation
Y. Okimoto et al., Reaction of homoallylic alcohols with NaIO4/NaHSO3 reagent - synthesis of alkyl substituted tetrahydrofuran derivatives, TETRAHEDR L, 41(52), 2000, pp. 10223-10227
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
52
Year of publication
2000
Pages
10223 - 10227
Database
ISI
SICI code
0040-4039(200012)41:52<10223:ROHAWN>2.0.ZU;2-L
Abstract
Treatment of homoallylic alcohols with NaIO4/NaHSO3 reagent in aqueous t-Bu OH under mild conditions produced tetrahydrofuran derivatives together with iodohydrins in a stereospecific manner. The reaction pathways of the forma tion of tetrahydrofurans from trans- and cis-homoallylic alcohols were foun d to be different. The present method provides a new approach to Various al kylated tetrahydrofuran derivatives. (C) 2000 Elsevier Science Ltd. All rig hts reserved.