'Naked sugars of the second generation': Asymmetric synthesis of long-chain polypropionates and analogues starting with acetone

Autor:	Philippe Kernen, Maciej Bialecki, A.‐F. Sevin, Pierre Vogel
Rok vydání:	1996
Předmět:	Stereocontrolled synthesis Chemistry Stereochemistry General Chemical Engineering Enantioselective synthesis chemistry.chemical_element General Chemistry Stereocenter Adduct chemistry.chemical_compound oxabicyclic compounds Acetone Organic chemistry Lithium Long chain
Zdroj:	Pure and Applied Chemistry. 68:719-722
ISSN:	1365-3075 0033-4545
DOI:	10.1351/pac199668030719
Popis:	Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)- or (1'S)-camphanate are transformed readily into polypropionate fragments containing four or five contiguous stereogenic centres. They can be condensed via cross-aldolizations to lithium enolates of 7-oxabicyclo[2.2.1]heptan-2-ones with high diastereoselectivity generating long-chain systems containing up to eleven stereogenic centres and tertiary alcoholic moieties.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::15bd18446a783309b3f0367651359882 https://doi.org/10.1351/pac199668030719 Zobrazit plný text záznamu