Asymmetric Synthesis of Fluorinated Flavanone Derivatives by an Organocatalytic Tandem Intramolecular Oxa-Michael Addition/Electrophilic Fluorination Reaction by Using Bifunctional Cinchona Alkaloids

被引：74

作者：

Wang, Hai-Feng ^{[1
]}

Cui, Hai-Feng ^{[1
]}

Chai, Zhuo ^{[1
]}

Li, Peng ^{[1
]}

Zheng, Chang-Wu ^{[1
]}

Yang, Ying-Quan ^{[2
]}

Zhao, Gang ^{[1
,2
]}

机构：

[1] Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 48期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cinchona alkaloids; domino reactions; fluorination; oxa-Michael addition; CATALYTIC ENANTIOSELECTIVE FLUORINATION; ESTROGEN-RECEPTOR LIGANDS; FRIEDEL-CRAFTS REACTION; ALPHA; BETA-UNSATURATED KETONES; ELECTROPHILIC FLUORINATION; CONJUGATE ADDITIONS; ALPHA-FLUORINATION; CARBONYL-COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; CHIRAL CATALYSTS;

D O I：

10.1002/chem.200902303

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

"Chemical Equation Presented" A bifunetional quinidine derivative, containing a trifluoromethyl group, was found to catalyze a tandem intramolecular oxa-Michael addition/electrophilic fluorination reaction of acti-vated α,β-unsaturated ketones (see scheme). A series of chiral fluorinated flavanone derivatives were obtained in excellent yields and with high enantioselectivities. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：13299 / 13303

页数：5

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