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
收藏
页码：1318 / 1321
页数：4
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