Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

被引：12

作者：

Greenwood, Phillip D. G. ^{[1
]}

Grenet, Erwann ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, BCH 4306, EPFL SB ISIC LCSO, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 12期

基金：

瑞士国家科学基金会;

关键词：

alkynes; amino alcohols; palladium catalysis; stereoselective synthesis; tethers; ATMOSPHERIC CO2; CARBOXYLATIVE CYCLIZATION; EFFICIENT SYNTHESIS; ALDEHYDES; AMINOCARBONYLATION; CARBOAMINATION; HYDROAMINATION; RUPINTRIVIR; BUPROPION; MECHANISM;

D O I：

10.1002/chem.201900020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,2-Amino alcohols and -aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or -amino ketones using hydrogenation or hydrolysis, respectively.

引用

页码：3010 / 3013

页数：4

共 53 条

[1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].