Rh-IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone

被引：19

作者：

Kuuloja, Noora ^{[1
]}

Vaismaa, Matti ^{[1
]}

Franzen, Robert ^{[1
]}

机构：

[1] Tampere Univ Technol, Chem Lab, Dept Chem & Bioengn, Tampere 33720, Finland

来源：

TETRAHEDRON | 2012年 / 68卷 / 10期

关键词：

CHIRAL DIENE LIGANDS; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; HECK-TYPE REACTION; ASYMMETRIC 1,4-ADDITION; ARYLBORONIC ACIDS; OLEFIN LIGANDS; BORONIC ACIDS; ROOM-TEMPERATURE; EFFICIENT; REAGENTS;

D O I：

10.1016/j.tet.2012.01.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2313 / 2318

页数：6

共 52 条

[1] New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium [J].

Amengual, R ;

Michelet, V ;

Genêt, JP .

TETRAHEDRON LETTERS, 2002, 43 (34) :5905-5908

[2] (R)-3,5-diCF3-SYNPHOS and (R)-p-CF3-SYNPHOS, Electron-Poor Diphosphines for Efficient Room Temperature Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids [J].

Berhal, Farouk ;

Esseiva, Olivier ;

Martin, Charles-Henri ;

Tone, Hitoshi ;

Genet, Jean-Pierre ;

Ayad, Tahar ;

Ratovelomanana-Vidal, Virginie .

ORGANIC LETTERS, 2011, 13 (11) :2806-2809

[3] ON PYRROLE OXIDATION WITH HYDROGEN PEROXIDE [J].

BOCCHI, V ;

CHIERICI, L ;

GARDINI, GP ;

MONDELLI, R .

TETRAHEDRON, 1970, 26 (17) :4073-&

[4] ANALOGS OF GAMMA-HYDROXYBUTYRIC ACID - SYNTHESIS AND BINDING-STUDIES [J].

BOURGUIGNON, JJ ;

SCHOENFELDER, A ;

SCHMITT, M ;

WERMUTH, CG ;

HECHLER, V ;

CHARLIER, B ;

MAITRE, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (05) :893-897

[5] Chiral Sulfoxide-Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium-Catalyzed Asymmetric Conjugate Additions [J].

Chen, Guihua ;

Gui, Jiangyang ;

Li, Liangchun ;

Liao, Jian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7681-7685

[6] Vicarious silylative mukaiyama aldol reaction: A vinylogous extension [J].

Curti, Claudio ;

Sartori, Andrea ;

Battistini, Lucia ;

Rassu, Gloria ;

Buffeddu, Paola ;

Zanardi, Franca ;

Casiraghi, Giovanni .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5446-5451

[7] Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].

Defieber, C ;

Paquin, JF ;

Serna, S ;

Carreira, EM .

ORGANIC LETTERS, 2004, 6 (21) :3873-3876

[8]

Diaz A, 1997, SYNTHESIS-STUTTGART, P559

[9] Highly practical catalytic asymmetric 1,4-addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0] diene ligands [J].

Feng, Chen-Guo ;

Wang, Zhi-Qian ;

Shao, Cheng ;

Xu, Ming-Hua ;

Lin, Guo-Qiang .

ORGANIC LETTERS, 2008, 10 (18) :4101-4104

[10] Simple N-Sulfinyl-Based Chiral Sulfur-Olefin Ligands for Rhodium-Catalyzed Asymmetric 1,4-Additions [J].

Feng, Xiangqing ;

Wang, Yazhou ;

Wei, Beibei ;

Yang, Jing ;

Du, Haifeng .

ORGANIC LETTERS, 2011, 13 (13) :3300-3303

← 1 2 3 4 5 6 →