Selective Catalytic Hydrogenations and Hydrogenolyses VIII [1]: Stereoselective Synthesis of the Stereomeric Pilopyl Alcohols

Autor:	Manfred Renz, Eberhard Reimann, Helene Unger
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Turn (biochemistry) chemistry.chemical_compound chemistry Yield (chemistry) Mineral acid Organic chemistry Alcohol Stereoselectivity General Chemistry Ethyl ester Catalysis
Zdroj:	Monatshefte f�r Chemie / Chemical Monthly. 133:1285-1290
ISSN:	1434-4475 0026-9247
Popis:	The stereoselective synthesis of pilopyl- and isopilopyl alcohol is reported. The reaction of dimethyldioxanone and diethoxyphosphoryl-butyric acid ethyl ester afforded the corresponding dioxanylidenbutyric acid ester as the key intermediate. Upon treatment with mineral acid it cyclized giving 3-ethyl-4-hydroxymethylfuran-2-one which in turn could be converted either to 3-ethyl-4-methylfuranone or pilopyl alcohol with excellent stereoselectivity and quantitative chemical yield. On the other hand, hydrogenation and subsequent cyclization of the same key compound furnished isopilopyl alcohol with good stereomeric purity and yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::91872bb25689ee1b79bbd8e8db6897e1 https://doi.org/10.1007/s00706-002-0484-9 Zobrazit plný text záznamu Full text from SpringerLink