CPBA 促进炔酰胺的β-氧化反应生成缩醛：在手性分子间转缩醛反应中的应用。
β-Oxidation of Ynamides into ,Acetals by CPBA: Application in Enantioselective Intermolecular Transacetalization.
机构信息
Department 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.
出版信息
Org Lett. 2019 Nov 15;21(22):9009-9013. doi: 10.1021/acs.orglett.9b03411. Epub 2019 Nov 6.
Oxidation of ynamides by CPBA led to β-oxygenation and resulted in formation of carbonyl compounds with α-,acetal functionality. These 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-,acetal. Subsequent diastereoselective transformations occurred with exceptional selectivity according to Felkin-Anh model.
CPBA 氧化炔酰胺导致 β-氧代化，并生成具有 α-、缩醛官能团的羰基化合物。这些缩醛以高产率形成，并且可以在室温下无限期储存。然而，它们可以被手性布朗斯台德酸激活，并经历对映选择性的转缩醛化生成 α-、缩醛。根据费尔金-安恩模型，随后的非对映选择性转化以优异的选择性发生。
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