Stereoselective Syntheses of α-Substituted Cyclic Ethers andsyn-1,3-Diols

Autor:	Teruaki Mukaiyama, Koichi Homma, Haruhiro Takenoshita
Rok vydání:	1990
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Silylation Nucleophile Diol Antimony pentachloride Organic chemistry General Chemistry Triethylsilane Trimethylsilyl cyanide Aliphatic compound Lactone
Zdroj:	Bulletin of the Chemical Society of Japan. 63:1898-1915
ISSN:	1348-0634 0009-2673
Popis:	In the presence of a catalytic amount of triphenylmethylium hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II) iodide, α-substituted cyclic ethers are stereoselectively prepared from lactones by successive treatment with 1-(t-butyldimethylsiloxy)-1-ethoxyethene and silyl nucleophiles such as triethylsilane, allyltrimethylsilane and trimethylsilyl cyanide. These catalysts also promote the reaction of γ-, δ-, and e-trimethylsiloxy carbonyl compounds with silyl nucleophiles resulting in the formation of α-substituted cyclic ethers. The former procedure is effectively applied to short syntheses of (−)-cis-rose oxide and (cis-6-methyltetrahydro-2-pyranyl)acetic acid, a constitutent of civet. Furthermore, syn-1,3-diols are also stereoselectively prepared from lactone analogue, 6-cis-substituted 2-trichloromethyl-1,3-dioxan-4-ones, easily prepared from β-hydroxy carboxylic acids.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4003efa5e627db0d38cbc950b5b579b6 https://doi.org/10.1246/bcsj.63.1898 Zobrazit plný text záznamu