Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals

被引：71

作者：

Lee, Ji-Woong ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 44期

基金：

欧洲研究理事会;

关键词：

SILYL ENOL ETHERS; SUBSTITUTED CARBONYL-COMPOUNDS; CHIRAL BRONSTED ACID; ENANTIOSELECTIVE PROTONATION; OPTICAL ACTIVATION; ENANTIOMERIC ENRICHMENT; DE-RACEMIZATION; DISILYL ACETALS; ESTERS; IDENTIFICATION;

D O I：

10.1021/ja3096202

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic alpha-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Bronsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5)(2)C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.

引用

页码：18245 / 18248

页数：4

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