Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals

被引：53

作者：

Li, Guo-Tai ^{[1
]}

Li, Zhi-Ke ^{[1
]}

Gu, Qing ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; ARYLBORONIC ACIDS; ACYL AZOLIUMS; LEWIS-ACID; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITIONS; MICHAEL ADDITION; QUINONE METHIDES; DELTA-LACTONES;

D O I：

10.1021/acs.orglett.7b00088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly enantioselective synthesis of 4-ary1-3,4-dihydrocoumarins was realized through direct annulation of phenols with enals catalyzed by dihydroisoquinoline-type NHC (DHIQ-NHC), an N-heterocyclic carbene derived from L-phenylalanine. The catalytic reaction proceeds with a wide scope of electron-rich phenols and enals providing structurally diverse 4-aryl-3,4-dihydrocoumarins in good to excellent yields and enantioselectivity. This method was useful in the synthesis of natural products and biologically relevant compounds from readily available starting materials.

引用

页码：1318 / 1321

页数：4

共 76 条

[31] Kinetic resolution of 4-substituted-3,4-dihydrocoumarins via Pd-catalyzed asymmetric allylic alkylation reaction: enantioselective synthesis of trans-3,4-disubstituted-3,4-dihydrocoumarins [J].