Stereoselective Synthesis of α-Alkylidene β-Oxo Amides by Palladium-Catalyzed Carbonylation

被引：24

作者：

Perrone, Serena ^{[1
]}

Salomone, Antonio ^{[2
,3
]}

Caroli, Antonio ^{[1
,3
]}

Falcicchio, Aurelia ^{[4
]}

Citti, Cinzia ^{[1
]}

Cannazza, Giuseppe ^{[5
]}

Troisi, Luigino ^{[1
]}

机构：

[1] Univ Salento, Dipartimento Sci & Tecnol Biol & Ambientali, I-73100 Lecce, Italy

[2] Univ Bari Aldo Moro, Dipartimento Farm Sci Farmaco, I-70125 Bari, Italy

[3] CINMPIS, I-70125 Bari, Italy

[4] CNR, IC, I-70125 Bari, Italy

[5] Univ Modena & Reggio Emilia, Dipartimento Sci Vita, I-41121 Modena, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 27期

关键词：

Homogeneous catalysis; Palladium; Carbonylation; Amides; ALCOHOLS; HETEROCYCLES; RUTHENIUM; AMINES; BOND;

D O I：

10.1002/ejoc.201402666

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct method to obtain -alkylidene -oxo amides by the palladium-catalyzed carbonylation of -chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the -alkylidene -oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl--lactam intermediate has also been proposed.

引用

页码：5932 / 5938

页数：7

共 38 条

[1]

[Anonymous], ANGEW CHEM

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