β-Oxidation of Ynamides into N,O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization

Autor:	Quynh H. Nguyen, Soumen Biswas, Nguyen H. Nguyen, Seunghoon Shin, Dilip V. Patil
Rok vydání:	2019
Předmět:	010405 organic chemistry Chemistry Organic Chemistry Intermolecular force Enantioselective synthesis food and beverages 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Physical and Theoretical Chemistry Selectivity Brønsted–Lowry acid–base theory
Zdroj:	Organic Letters. 21:9009-9013
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.9b03411
Popis:	Oxidation of ynamides by mCPBA led to β-oxygenation and resulted in formation of carbonyl compounds with α-N,O-acetal functionality. These N,O-acetals are formed in high yields and can be stored indefinitely at room temperature. Yet, they can be activated by a chiral Bronsted acid and underwent an enantioselective transacetalization into a α-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d427af1c2af7073f74c87cc6add93532 https://doi.org/10.1021/acs.orglett.9b03411 Zobrazit plný text záznamu