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
收藏
页码：6856 / 6859
页数：4
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