A short route to homochiral D- and L-hexose precursors from (R)-methyl-p-tolylsulfoxide

Autor:	María-Eugenia Blanco, J. M. Llera, Felipe Alcudia, Mariana Trujillo
Rok vydání:	1994
Předmět:	chemistry.chemical_classification Stereochemistry Pummerer rearrangement Organic Chemistry Carbonyl reduction Sulfoxide Condensation reaction Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Stereoselectivity Hexose Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 5:709-716
ISSN:	0957-4166
Popis:	Homochiral D - and L -hexose precursors have been prepared in good overall yield from ( R )-methyl- p -tolylsulfoxide as the sole asymmetric inductor. The process involves sequential condensation of the sulfoxide with ethyl 2-furancarboxylate, stereoselective sulfoxide-monitored carbonyl reduction, Pummerer rearrangement of the sulfinyl group, reduction of the resulting aldehydes and ring-oxidation of the corresponding furfuryl alcohols.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bd2a0c8b708c3c8796755e94e01d600d https://doi.org/10.1016/0957-4166(94)80033-2 Zobrazit plný text záznamu