ChemInform Abstract: (Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2]-Wittig Rearrangement

Autor:	Takeo Nakano, Fumiya Kurosawa, Yutaka Ukaji, Takahiro Soeta, Kohei Endo
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Allylic rearrangement chemistry Stereoselectivity General Medicine 1 2-Wittig rearrangement Medicinal chemistry Enol Coupling reaction
Zdroj:	ChemInform. 46
ISSN:	0931-7597
DOI:	10.1002/chin.201542039
Popis:	The stereoselective transformation of α-alkoxyacetoaldehydes to the corresponding (Z)-vinyl triflates was achieved by treatment with phenyl triflimide and DBU. The stereochemistry was explained by the “syn-effect,” which was attributed primarily to an σ → π* interaction. The β-alkoxy vinyl triflates obtained were applied to the stereoselective synthesis of structurally diverse (Z)-allylic alcohols via transition metal-catalyzed cross-coupling reaction and [1,2]-Wittig rearrangement.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::33e17fdda1520b13effb46dfe9762c16 https://doi.org/10.1002/chin.201542039 Zobrazit plný text záznamu Plný text