Development of a palladium catalyzed addition of boronic acids to alkynyl esters: synthesis of trisubstituted olefins as single isomers

被引：13

作者：

Bush, Alexander Graham ^{[1
]}

Jiang, Jojo Liu ^{[1
]}

Payne, Philippa R. ^{[1
]}

Ogilvie, William W. ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

TETRAHEDRON | 2009年 / 65卷 / 41期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BAYLIS-HILLMAN ADDUCTS; ORGANOBORONIC ACIDS; ARYLBORONIC ACIDS; STEREOSPECIFIC SYNTHESIS; CONJUGATE ADDITION; RHODIUM; HYDROARYLATION; REAGENTS; ALKENES; 1,1-DICHLORO-1-ALKENES;

D O I：

10.1016/j.tet.2009.08.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Very small phosphine ligands allow access to single isomer trisubstituted olefins from alkynyl esters with complete control of both stereochemistry and regiochemistry. This method provides a convenient synthesis of single isomer trisubstituted olefins without requiring olefin templates. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：8502 / 8506

页数：5

共 40 条

[1] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[2] A NEW STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED AND TETRASUBSTITUTED OLEFINS . CONJUGATE ADDITION OF DIALKYLCOPPER-LITHIUM REAGENTS TO ALPHA,BETA-ACETYLENIC ESTERS [J].

COREY, EJ ;

KATZENEL.JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (07) :1851-&

[3] Olefin metathesis [J].

Grubbs, RH .

TETRAHEDRON, 2004, 60 (34) :7117-7140

[4] Pd-catalyzed addition of organoboronic acids to alkynes at room temperature [J].

Gupta, AK ;

Kim, KS ;

Oh, CH .

SYNLETT, 2005, (03) :457-460

[5] Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].

Hayashi, T ;

Inoue, K ;

Taniguchi, N ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919

[6] Single-isomer iodochlorination of alkynes and chlorination of alkenes using tetrabutylammonium iodide and dichloroethane [J].

Ho, Michael L. ;

Flynn, Alison B. ;

Ogilvie, William W. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :977-983

[7] Phosphorylated aldehydes:: Preparations and synthetic uses [J].

Iorga, B ;

Eymery, F ;

Mouriès, V ;

Savignac, P .

TETRAHEDRON, 1998, 54 (49) :14637-14677

[8] Pd-catalyzed cross-coupling of Baylis-Hillman acetate adducts with bis(pinacolato)diboron: An efficient route to functionalized allyl borates [J].

Kabalka, GW ;

Venkataiah, B ;

Dong, G .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5807-5809

[9] Palladium-catalyzed cross-coupling of acetates of Bbaylis-Hillman adducts and potassium organotrifluoroborates [J].

Kabalka, GW ;

Venkataiah, B ;

Dong, G .

ORGANIC LETTERS, 2003, 5 (21) :3803-3805

[10] Suzuki-Miyaura approach to JNJ-26076713, an orally active tetrahydroquinoline-containing αVβ3/αVβ5 integrin antagonist.: Enantioselective synthesis and stereochemical studies [J].

Kinney, William A. ;

Teleha, Christopher A. ;

Thompson, Andrew S. ;

Newport, Maria ;

Hansen, Ryan ;

Ballentine, Scott ;

Ghosh, Shyamali ;

Mahan, Andrew ;

Grasa, Gabriela ;

Zanotti-Gerosa, Antonio ;

Dingenen, Jules ;

Schubert, Carsten ;

Zhou, Yong ;

Leo, Gregory C. ;

McComsey, David F. ;

Santulli, Rosemary J. ;

Maryanoff, Bruce E. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2302-2310

← 1 2 3 4 →