Phosphine-Catalyzed Asymmetric Intermolecular Cross-Vinylogous Rauhut-Currier Reactions of Vinyl Ketones with para-Quinone Methides

被引：152

作者：

Li, Shenhuan ^{[1
]}

Liu, Yuanyuan ^{[1
]}

Huang, Ben ^{[1
]}

Zhou, Tao ^{[1
]}

Tao, Hongmei ^{[1
]}

Xiao, Yuanjing ^{[1
]}

Liu, Lu ^{[1
]}

Zhang, Junliang ^{[1
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

来源：

ACS CATALYSIS | 2017年 / 7卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Rauhut-Currier reaction; 1,6-conjugated addition; organocatalysis; chiral phosphines; para-quinone methides; MORITA-BAYLIS-HILLMAN; 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; DOMINO REACTION; CONJUGATE ADDITIONS; FACILE STRATEGY; 4+2 ANNULATION; ACID-ESTERS; ADDITION/AROMATIZATION; CONSTRUCTION;

D O I：

10.1021/acscatal.7b00030

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A chiral amide-phosphine bifunctional catalyst was developed and successfully applied to the asymmetric intermolecular cross-vinylogous Rauhut-Currier of alkyl vinyl ketones with para-quinone methides, offering excellent regioselectivity and stereoselectivity (up to >99% enantiomeric excess (ee)). This method provides a facile access to structurally diverse widely existed diarylmethine stereogenic centers with excellent enantioselectivity. Density functional theory (DFT) calculations have been performed to understand the mechanism and enantioselectivity for this phosphinecatalyzed asymmetric transformation.

引用

页码：2805 / 2809

页数：5

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