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Updated: Jan 4, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
β-Oxidation of Ynamides into N,O-Acetals by mCPBA: Application in Enantioselective Intermolecular Transacetalization
Nguyen H Nguyen1, Quynh H Nguyen1, Soumen Biswas1
1Department of Chemistry, Research Institute for Natural Sciences and Center for New Directions in Organic Synthesis (CNOS) , Hanyang University , 222 Wangsimni-ro , Seongdong-gu, Seoul 04763 , Korea.
Abstract:
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 Brønsted acid and underwent an enantioselective transacetalization into a α-N,O-acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.
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