Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl-ynamides into 3,6-Dihydropyridinones

被引：25

作者：

Febvay, Julie ^{[1
]}

Sanogo, Youssouf ^{[1
]}

Retailleau, Pascal ^{[1
]}

Gogoi, Manash Protim ^{[2
]}

Sahoo, Akhila K. ^{[2
]}

Marinetti, Angela ^{[1
]}

Voituriez, Arnaud ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS,UPR 2301, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France

[2] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

关键词：

CATALYZED INTERMOLECULAR OXIDATION; YNE-TETHERED YNAMIDE; GOLD CATALYSIS; CARBENES; ACCESS; ALKYNES;

D O I：

10.1021/acs.orglett.9b02644

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study discloses the first enantioselective variant of the gold(I)-catalyzed hydrative cyclizations of ynamides, which have been implemented by using bis-gold(I) complexes of chiral diphosphines. Starting from N-propargyl-ynamides and water in the presence of p-toluenesulfonic acid, the cyclization reactions afford N-tosyl-3,6-dihydropyridin-2(1H)-ones in good isolated yields and with high levels of stereocontrol (20 examples, enantiomeric ratios up to 94:6).

引用

页码：9281 / 9285

页数：5

共 56 条

[1] Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals [J].