One-Pot Asymmetric Synthesis of Substituted Tetrahydrofurans via a Multicatalytic Benzoin/Michael/Acetalization Cascade

被引：18

作者：

He, Gu ^{[1
]}

Wu, Fengbo ^{[1
]}

Huang, Wei ^{[1
,2
]}

Zhou, Rui ^{[1
]}

Ouyang, Liang ^{[1
]}

Han, Bo ^{[1
,2
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

[2] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Sch Pharm, Chengdu 611137, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 10期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

asymmetric synthesis; domino reactions; heterocycles; multicomponent reactions; organocatalysis; CATALYZED DOMINO REACTIONS; N-HETEROCYCLIC CARBENES; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ALDEHYDES; CARBONYL-COMPOUNDS; TANDEM REACTIONS; ORGANOCATALYSIS; METAL; SPIROLACTONIZATION; CONDENSATION;

D O I：

10.1002/adsc.201400172

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A sequential benzoin/Michael/acetalization tandem reaction catalyzed by NHC and amine together has been developed to assemble aromatic aldehydes and enals into chiral tetrahydrofuran derivatives bearing multiple functional groups and stereogenic centers with high stereoselectivity of up to 95: 5 dr and 96% ee. The high yield and stereocontrol of this process may be due to both acid-promoted symmetrization of racemic acyloins and iminium ion activation of enals.

引用

页码：2311 / 2319

页数：9

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