Intervention of catalytic amounts of water in the allylic rearrangements of glycal derivatives

Autor:	Richard H. Furneaux, Regine Blattner, Robert J. Ferrier
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Allylic rearrangement Glycal Thiophenol Organic Chemistry Diastereomer Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Glucal
Zdroj:	Tetrahedron: Asymmetry. 11:379-383
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(99)00499-1
Popis:	It is confirmed that tri- O -acetyl- d -glucal with thiophenol in the presence of BF 3 ·OEt 2 as catalyst gives the allylically rearranged S -phenyl 4,6-di- O -acetyl-2,3-dideoxy-1-thio-α- and β- d - erythro -hex-2-enopyranosides as the main products, and now demonstrated that the presence of catalytic proportions of water diverts the reaction in favour of the isomeric S -phenyl 4,6-di- O -acetyl-2-deoxy-3-phenylthio-1-thio- d - arabino - and - d - ribo -hexopyranosides. It is proposed that these products are formed from an intermediate enal.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ed51032a0f8a8cebd850fd8eb5217af2 https://doi.org/10.1016/s0957-4166(99)00499-1 Zobrazit plný text záznamu Full Text from ScienceDirect