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 50 条

[1] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
Schmink, Jason R.
Krska, Shane W.
Tudge, Matthew T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[2] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
ALHASSAN, MI
SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
[3] Palladium-catalyzed cross-coupling of benzyl thioacetates and aryl halides
Wager, Krista M.
Daniels, Matthew
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[4] Palladium-catalyzed cross-coupling reaction of alkyltrifluorosilanes with aryl halides
Matsuhashi, H
Asai, S
Hirabayashi, K
Mori, A
Hiyama, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (02) : 437 - 444
[5] Palladium-Catalyzed Cross-Coupling of Benzyl Thioacetates and Aryl Halides
Wager, Krista M.
Daniels, Matthew H.
ORGANIC LETTERS, 2011, 13 (15) : 4052 - 4055
[6] Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides
Matsuhashi, H.
Asai, S.
Hirabayashi, K.
Hatanaka, Y.
Bulletin of the Chemical Society of Japan, 70 (02):
[7] POLY(ARYL KETONES) VIA PALLADIUM-CATALYZED CROSS-COUPLING
MOORE, JS
MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1992, 13 (02): : 91 - 96
[8] Palladium-catalyzed cross-coupling reactions of aryl mesylates
So, Chau Ming
Kwong, Fuk Yee
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4963 - 4972
[9] Palladium-catalyzed homocoupling and cross-coupling reactions of Aryl halides in poly(ethylene glycol)
Wang, LA
Zhang, YH
Liu, LF
Wang, YG
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1284 - 1287
[10] Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides
Denmark, SE
Baird, JD
ORGANIC LETTERS, 2004, 6 (20) : 3649 - 3652

← 1 2 3 4 5 →