Diastereoselective synthesis of 1-allyl and 1,2-bis(allyl)-1,2-diols: Versatile synthons for substituted tetrahydrofuran derivatives

Citation
S. Kumar et al., Diastereoselective synthesis of 1-allyl and 1,2-bis(allyl)-1,2-diols: Versatile synthons for substituted tetrahydrofuran derivatives, SYNLETT, (9), 2001, pp. 1431-1433
Citations number
24
Language
INGLESE
art.tipo
Letter
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
0936-5214 → ACNP
Issue
9
Year of publication
2001
Pages
1431 - 1433
Database
ISI
SICI code
0936-5214(200109):9<1431:DSO1A1>2.0.ZU;2-3
Abstract
Hydroxy ketones and 2-ketoaldehydes undergo indium mediated highly diastere oselective mono and bis-allylation reactions to give respective 1-allyl 2a- c and 1,2-bis (allyl)- 7a-c 1,2 diols. 2a undergoes I-2 / NaHCO3 and m-CPBA mediated diastereoselective intramolecular cyclizations to provide respect ive (2S*, 3R*. 5S*)-2,3-diphenyl-4-hydroxy-5-iodo methyltetrahydrofuran 4a and (2S*, 3R*, 5R*)-2,3-diphenyl-4-hydroxy-5-hydroxymethyl tetrahydrofuran 5b as major product.