Development of Chiral Terminal-Alkene-Phosphine Hybrid Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions

被引：106

作者：

Liu, Zhaoqun ^{[1
]}

Du, Haifeng ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

基金：

美国国家科学基金会;

关键词：

DIENE LIGANDS; OLEFIN LIGANDS; 1,4-ADDITION; ETHERIFICATION; ALKYLATIONS; COMPLEXES; ADDITIONS; ALCOHOLS; DESIGN;

D O I：

10.1021/ol101069y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of novel chiral terminal-alkene phosphine hybrid ligands were successfully developed from diethyl L-tartrate for palladium-catalyzed asymmetric allylic alkylations, etherifications, and amination to give the desired products in excellent yields and ee's.

引用

收藏

页码：3054 / 3057

页数：4

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[1] ALKYLATIVE EPOXIDE REARRANGEMENT - A STEREOSPECIFIC APPROACH TO CHIRAL EPOXIDE PHEROMONES [J].

BELL, TW ;

CIACCIO, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5153-5162

[2] Catalytic Enantioselective Formation of Chiral-Bridged Dienes Which Are Themselves Ligands for Enantioselective Catalysis [J].

Brown, M. Kevin ;

Corey, E. J. .

ORGANIC LETTERS, 2010, 12 (01) :172-175

[3] Phosphinite Thioethers Derived from Chiral Epoxides. Modular P,S-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J].

Caldentey, Xisco ;

Pericas, Miguel A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) :2628-2644

[4]

Deblon S., 2003, [No title captured], Patent No. [03048175, WO 03/048175 Al]

[5] Chiral olefins as steering ligands in asymmetric catalysis [J].

Defieber, Christian ;

Gruetzmacher, Hansjoerg ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502

[6] Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: Sulfamic acid as amonia equivalent [J].

Defieber, Christian ;

Ariger, Martin A. ;

Moriel, Patricia ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3139-3143

[7] Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions [J].

Duan, Wei-Liang ;

Iwamura, Hiroshi ;

Shintani, Ryo ;

Hayashi, Tamio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :2130-2138

[8] Allylic Amination by a DNA-Diene-Iridium(I) Hybrid Catalyst [J].

Fournier, Pierre ;

Fiammengo, Roberto ;

Jaeschke, Anders .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4426-4429

[9] Recombinant HDL-like nanoparticles: A specific contrast agent for MRI of atherosclerotic plaques [J].

Frias, JC ;

Williams, KJ ;

Fisher, EA ;

Fayad, ZA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16316-16317

[10] C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions [J].

Gendrineau, Thomas ;

Chuzel, Olivier ;

Eijsberg, Hendrik ;

Genet, Jean-Pierre ;

Darses, Sylvain .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7669-7672

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