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Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene.
Organic Letters ( IF 5.2 ) Pub Date : 2020-01-08 , DOI: 10.1021/acs.orglett.9b04232
Surojit Santra 1 , Ujjwal Maji 1 , Joyram Guin 1
Affiliation  

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Brønsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

中文翻译:

N-杂环卡宾催化的无环1,3-二羰基的对映选择性α-氨基化。

在这里,我们描述了一种用于α-取代的无环1,3-酮酰胺和1,3-酰胺基酯的催化对映选择性α-氨基化的方法,该方法提供了具有N-取代的季立体中心和手性N-杂环卡宾(NHC)的产物。该反应基于利用NHC的固有布朗斯台德碱特性,该特性使能催化形成包含烯醇盐和the离子的手性离子对。通过该方法将一系列具有挑战性的开链α-取代的1,3-二羰基胺化,其ee≤99%。
更新日期:2020-01-09
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