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

Martín Avalos, Reyes Babiano, Pedro Cintas, Fernando R. Clemente, Ruth Gordillo, Michael B. Hursthouse, José L. Jiménez, Mark E. Light, Juan C. Palacios

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Chiral dihydrothiophenes derived from carbohydrates can be transformed into a novel class of bicyclic and highly functionalized chirons by treatment with NaH. A mechanistic rationale is proposed which is consistent with experimental observations and demonstrates the stereodiscriminating properties exerted by carbohydrate chains with different configurations.

Original languageEnglish (US)
Pages (from-to)2261-2264
Number of pages4
JournalTetrahedron Asymmetry
Volume12
Issue number16
DOIs
StatePublished - Sep 13 2001

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Avalos, M., Babiano, R., Cintas, P., Clemente, F. R., Gordillo, R., Hursthouse, M. B., Jiménez, J. L., Light, M. E., & Palacios, J. C. (2001). Carbohydrates as chiral controllers: Synthesis of dihydrothieno[2,3-c]furanones. Tetrahedron Asymmetry, 12(16), 2261-2264. https://doi.org/10.1016/S0957-4166(01)00408-6