Enantioselective Synthesis of 4-Substituted Dihydrocoumarins through a Zinc Bis(hydroxyamide)-Catalyzed Conjugate Addition of Terminal Alkynes

被引：40

作者：

Blay, Gonzalo ^{[1
]}

Carmen Munoz, M. ^{[2
]}

Pedro, Jose R. ^{[1
]}

Sanz-Marco, Amparo ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Valencia, Spain

[2] Univ Politecn Valencia, Dept Fis Aplicada, E-46022 Valencia, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 06期

关键词：

alkynylation; asymmetric catalysis; N; O ligands; nucleophilic addition; oxygen heterocycles; ASYMMETRIC-SYNTHESIS; BIOLOGICAL EVALUATION; DIALKYLZINC REAGENTS; COMPLEX FLAVONOIDS; FARINOSE EXUDATE; SILYLACETYLENES; 1,4-ADDITION; ALKYNYLATION; DERIVATIVES; MYCOTOXINS;

D O I：

10.1002/adsc.201201120

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new enantioselective catalyst for the conjugate addition of terminal alkynes has been developed. Terminal alkynes react with 3-alkoxycarbonylcoumarins in the presence of diethylzinc and bis(hydroxyamide) ligands to give chiral non-racemic dihydrocoumarins substituted with an alkynyl group on the C-4 position with good yields and enantiomeric excesses up to 95%.

引用

页码：1071 / 1076

页数：6

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