N-Alkoxyacrylamides in Domino Reactions: Catalytic and Stereoselective Access to δ-Lactams

被引：20

作者：

Champetter, Philippe ^{[1
]}

Castillo-Aguilera, Omar ^{[1
]}

Taillier, Catherine ^{[1
]}

Briere, Jean-Francois ^{[2
]}

Dalla, Vincent ^{[1
]}

Oudeyer, Sylvain ^{[2
]}

Comesse, Sebastien ^{[1
]}

机构：

[1] Normandie Univ, UNILEHAVRE, CNRS, FR 3038,URCOM, F-76600 Le Havre, France

[2] Normandie Univ, UNIROUEN, INSA Rouen, CNRS,COBRA, F-76000 Rouen, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 47期

关键词：

Domino reactions; N-alkoxyacrylamides; Stereoselective synthesis; delta-Lactams; Catalysis; MICHAEL REACTION; GAMMA-LACTAMS; ALPHA; BETA-UNSATURATED AMIDES; SUBSTITUTED PIPERIDINONES; ASYMMETRIC-SYNTHESIS; AMINES; DERIVATIVES;

D O I：

10.1002/ejoc.201901528

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first domino aza-Michael/intramolecular-Michael reaction employing acrylamides as key ambivalent partners for the synthesis of delta-lactams is presented. It has been shown that the desired reactivity is contingent to the presence of an N-alkoxy group within the acrylamides. Thus, in a base-catalyzed process that operates under mild conditions, N-alkoxyacrylamides are readily converted into polysubstituted delta-lactams in good yields with good to excellent stereocontrol.

引用

页码：7703 / 7710

页数：8

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