Vinylethylene Carbonates as α,β-Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition

Autor:	Zhiqiang Zhang, Weibo Yang, Yu-wen Yang, Yi Xu, Lu Chen
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Decarboxylation Organic Chemistry Synthon Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Aldehyde Cycloaddition 0104 chemical sciences Ring size chemistry Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 21:6674-6678
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.9b02266
Popis:	Herein, we report a novel stepwise addition-controlled ring size method, to access tetrahydropyrimidines through an operationally simple [3 + 3] cycloaddition of vinylethylene carbonates with triazinanes. Interestingly, we could also use this method for a [3 + 3] oxidative cycloaddition, which allows the facile synthesis of polysubstituted terphenyls under mild conditions. Mechanistic studies suggest that vinylethylene carbonates could generate α,β-unsaturated aldehydes as 3-carbon synthons for cycloaddition via a combination process of Pd-catalyzed decarboxylation and β-H elimination.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e3bc9dc7ba4dc83203243d4754832886 https://doi.org/10.1021/acs.orglett.9b02266 Zobrazit plný text záznamu