Intermolecular Rhodium(II)-Catalyzed Allylic C(sp3)-H Amination of Cyclic Enamides

被引：13

作者：

Rey-Rodriguez, Romain ^{[1
,2
]}

Jestin, Gregory ^{[1
]}

Gandon, Vincent ^{[2
,3
]}

Grelier, Gwendal ^{[2
]}

Retailleau, Pascal ^{[2
]}

Darses, Benjamin ^{[2
]}

Dauban, Philippe ^{[2
]}

Gillaizeau, Isabelle ^{[1
]}

机构：

[1] Univ Orleans, Inst Organ & Analyt Chem, ICOA UMR CNRS 7311, Rue Chartres, F-45100 Orleans, France

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

[3] Univ Paris Saclay, Univ Paris Sud, CNRS UMR 8182, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 03期

关键词：

allylic amination; enamides; heterocycles; nitrenes; rhodium catalysis; C-H AMINATION; COMPLEX-MOLECULES; BONDS; CATALYST; FUNCTIONALIZATION; AZIRIDINATION; OXIDATION; NITRENES; ALKENYLATION; OXYAMIDATION;

D O I：

10.1002/adsc.201701188

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The intermolecular rhodium(II)-catalyzed C(sp(3))-H amination of enamides gives access to new 4-aminopiperidine derivatives that are useful building blocks in medicinal chemistry. This efficient transformation proceeds at room temperature with complete regio- and chemoselectivity in favor of the allylic C(sp(3))-H bond, and has a broad functional group tolerance. In addition, the matched combination of the chiral complex Rh-2(S-nta)(4) [nta=(S)-N-1,8-naphthoylalanine] with an optically pure (S)-sulfonimidamide allows the isolation of allylic amines with excellent stereocontrol.

引用

页码：513 / 518

页数：6

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