Sc(OTf)3-Catalyzed C–C Bond-Forming Reaction of Cyclic Peroxy Ketals for the Synthesis of Highly Functionalized 1,2-Dioxene Endoperoxides

Autor:	Pengkang Liu, Lin Hu, Yukun Zhao, Haowei Feng
Rok vydání:	2021
Předmět:	Silylation 010405 organic chemistry Chemistry Organic Chemistry Ketene 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Enol 0104 chemical sciences Catalysis chemistry.chemical_compound Physical and Theoretical Chemistry Trimethylsilyl cyanide
Zdroj:	Organic Letters. 23:1632-1637
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c00056
Popis:	A new and general Sc(OTf)3-catalyzed C-C bond-forming reaction of 3-(2-methoxyethoxy)-endoperoxy ketals with silyl ketene acetals, silyl enol ethers, allyltrimethylsilane, and trimethylsilyl cyanide has been developed via the reactive peroxycarbenium ions, affording a wide range of complicated 3,3,6,6-tetrasubstituted 1,2-dioxenes bearing adjacent quaternary carbons and 3-acetyl/allyl/cyano functional groups in good yields at room temperature. Notably, the resultant 1,2-dioxenes are structurally stable, which can be facially transformed into another important 1,2-dioxane endoperoxide under conventional hydrogenation conditions without deconstructing the weak O-O bond.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f9d7785c42da62cf78393e912a74caf8 https://doi.org/10.1021/acs.orglett.1c00056 Zobrazit plný text záznamu