(-)-Methyl Cucurbate and (-)-Methyl Jasmonate by Kinetic Resolution

Autor:	Claudia Borm, Ekkehard Winterfeldt
Rok vydání:	2006
Předmět:	Cyclopentenone Methyl jasmonate Organic Chemistry Pyridinium chlorochromate General Chemistry Alkylation Borohydride Catalysis Adduct Kinetic resolution chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Liebigs Annalen. 1996:1209-1212
ISSN:	1099-0690 0947-3440
Popis:	The kinetic resolution of a malonate-substituted cyclopentenone gave rise to the formation of an enantiopure Diels-Alder adduct which was converted into methyl dehydrocucurbate 2 by diastereoselective alkylation with (Z)-1-bromo-2-pentene and subsequent borohydride reduction. Selective hydrogenation of 2 with a palladium/calcium carbonate catalyst proved to be a reliable route to (–)-methyl cucurbate (1) the oxidation of which with pyridinium chlorochromate and subsequent treatment with acid afforded (–)-methyl jasmonate (9).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::217f2560bf98a126c8349f01cb15691f https://doi.org/10.1002/jlac.199619960722 Zobrazit plný text záznamu Plný text