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

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