(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, Kohei Endo, Takahiro Soeta
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Allylic rearrangement chemistry Stereochemistry Organic Chemistry Stereoselectivity 1 2-Wittig rearrangement Enol Coupling reaction
Zdroj:	The Journal of organic chemistry. 80(11)
ISSN:	1520-6904
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. © 2015 American Chemical Society.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9964a644bb9f6067376ce45700376ffd https://pubmed.ncbi.nlm.nih.gov/25970239 Zobrazit plný text záznamu