Solvent-Enhanced Diastereo- and Regioselectivity in the PdII-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles via cis-Aminopalladation

被引：17

作者：

Balazs, Arpad ^{[1
]}

Hetenyi, Anasztazia ^{[1
]}

Szakonyi, Zsolt ^{[1
]}

Sillanpaa, Reijo ^{[3
]}

Fulop, Ferenc ^{[1
,2
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Stereochem Res Grp, Hungarian Acad Sci, H-6720 Szeged, Hungary

[3] Univ Jyvaskyla, Dept Chem, SF-40351 Jyvaskyla, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 30期

关键词：

allylic compounds; amination; domino reactions; oxidation; palladium; AZA-WACKER REACTIONS; MOLECULAR-OXYGEN; C-N; INTRAMOLECULAR AMINOPALLADATION; OXIDATIVE AMINATION; ORGANIC-CHEMICALS; BOND FORMATION; AMINO-ACIDS; ALKENES; CYCLIZATION;

D O I：

10.1002/chem.200900477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Pd-II-catalyzed intramolecular oxidative cyclization of tosyl-protected cis- and trans-N-allyl-2-aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane-fused pyrimidin-4-ones and 1,5-diazocin-6-ones were developed. In the course of the research, a marked solvent effect was observed on both the regio- and diastereoselectivity. Additionally, a novel Pd-II-mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis-aminopalladation mechanism.

引用

页码：7376 / 7381

页数：6

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