Carbohydrates as chiral controllers: synthesis of dihydrothieno[2,3-c]furanones

Authors
Avalos, M Babiano, R Cintas, P Clemente, FR Gordillo, R Hursthouse, MB Jimenez, JL Light, ME Palacios, JC
Citation
M. Avalos et al., Carbohydrates as chiral controllers: synthesis of dihydrothieno[2,3-c]furanones, TETRAHEDR-A, 12(16), 2001, pp. 2261-2264
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
16
Year of publication
2001
Pages
2261 - 2264
Database
ISI
SICI code
0957-4166(20010913)12:16<2261:CACCSO>2.0.ZU;2-N
Abstract
Chiral dihydrothiophenes derived from carbohydrates can be transformed into a novel class of bicyclic and highly functionalized chirons by treatment w ith NaH. A mechanistic rationale is proposed which is consistent with exper imental observations and demonstrates the stereodiscriminating properties e xerted by carbohydrate chains with different configurations. (C) 2001 Elsev ier Science Ltd. All rights reserved.