Chiral tetrahydrofuran synthesis from D-ribose diphenyl dithioacetal

Authors
Norris, P
Citation
P. Norris, Chiral tetrahydrofuran synthesis from D-ribose diphenyl dithioacetal, HETEROCYC C, 5(2), 1999, pp. 113-114
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLIC COMMUNICATIONS
ISSN journal
07930283 → ACNP
Volume
5
Issue
2
Year of publication
1999
Pages
113 - 114
Database
ISI
SICI code
0793-0283(1999)5:2<113:CTSFDD>2.0.ZU;2-H
Abstract
Treatment of D-ribose diphenyl dithioacetal 1 with 4.2 equivalents of rr-CP BA results in formation of the bis(phenylsulfone) 4, which is likely the re sult of an oxidation-elimination-cyclization sequence. Tetrahydrofuran 4 is protected as the isopropylidene derivative 5. The latter is alkylated to g enerate 6 and 5 undergoes reductive elimination to the olefin 7.