Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins

被引：63

作者：

Hack, Daniel ^{[1
]}

Chauhan, Pankaj ^{[1
]}

Deckers, Kristina ^{[1
]}

Hermann, Gary N. ^{[1
]}

Mertens, Lucas ^{[1
]}

Raabe, Gerhard ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

基金：

欧洲研究理事会;

关键词：

CYCLIC 1,3-DICARBONYL COMPOUNDS; FRIEDEL-CRAFTS ALKYLATION; CINCHONA ALKALOIDS; TANDEM REACTION; VITAMIN-K; 4-HYDROXYCOUMARIN; DERIVATIVES; WARFARIN; ALPHA; FUNCTIONALIZATION;

D O I：

10.1021/ol502551u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

引用

页码：5188 / 5191

页数：4

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