Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides

被引：110

作者：

Barluenga, Jose ^{[1
]}

Escribano, Maria ^{[1
]}

Aznar, Fernando ^{[1
]}

Valdes, Carlos ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 38期

关键词：

allyl amines; chiral ketones; cross-coupling; hydrazones; palladium; CARBENE INSERTION; VINYL HALIDES; HECK REACTION; DIAZOESTERS;

D O I：

10.1002/anie.201003450

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Papa was a rollin' ketone: Arylation of ketones with preservation of the chirality in configurationally unstable α-chiral ketones has been achieved by the palladium-catalyzed cross-coupling reaction between tosylhydrazones and aryl halides (see scheme; Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl). The regioselectivity in the β-hydride elimination step is key for the retention of configuration. © 2010 Wiley-VCH Verlag GmbH &. Co. KGaA, Weinheim.

引用

页码：6856 / 6859

页数：4

共 32 条

[1] Barluenga J., 2007, Angew. Chem, V119, P5683
[2] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines
Barluenga, Jose
Tomas-Gamasa, Maria
Moriel, Patricia
Amar, Fernando
Valdes, Carlos
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4792 - 4795
[3] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
Barluenga, José
Moriel, Patricia
Valdes, Carlos
Aznar, Fernando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
[4] Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
Barluenga, Jose
Escribano, Maria
Moriel, Patricia
Aznar, Fernando
Valdes, Carlos
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) : 13291 - 13294
[5] σ-Alkylpalladium Intermediates in Intramolecular Heck Reactions:Isolation and Catalytic Activity
Beccalli, Egle M.
Borsini, Elena
Brenna, Stefano
Galli, Simona
Rigamonti, Micol
Broggini, Gianluigi
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1670 - 1678
[6] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[7] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8] Enantioselective synthesis of six-membered palladacycles having metal-bound stereogenic carbons:: Isolation and reactivity of palladacycles containing readily accessible β-hydrogens
Burke, BJ
Overman, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (51) : 16820 - 16833
[9] Carey F.A., 2007, ADV ORGANIC CHEM A, P546
[10] CARIEIRA EM, 1999, COMPREHENSIVE ASYMME, V3

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