Room Temperature Highly Enantioselective Nickel-Catalyzed Hydrovinylation

被引：44

作者：

Lassauque, Nicolas ^{[1
]}

Francio, Giancarlo ^{[1
]}

Leitner, Walter ^{[1
]}

机构：

[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Tech & Makromol Chem, D-52074 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 18期

关键词：

asymmetric catalysis; C-C coupling; olefin dimerization; phosphoramidite ligands; ASYMMETRIC HYDROVINYLATION; CHIRAL PHOSPHORAMIDITE; LIGANDS; COORDINATION; SELECTIVITY; 1,3-DIENES; COMPLEXES; PALLADIUM; PROTOCOL; ROUTE;

D O I：

10.1002/adsc.200900559

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

At room temperature, nickel catalysts based on the new phosphoramidite (11bR)-N-[(S)-1-(naphthalen-1-yl)ethyl]-N-[(S)-1-(naphthalen-2yl)ethyl]dinaphtho[2,1'-d:1',2'-f] [1,3,2]dioxaphosphepin-4-amine provide excellent selectivities for 3-arylbut-1-enes (93-99%) with high enantioselectivities (90-95% ee) and TOFs (up to 8300 h(-1)) in the hydrovinylation of electron-rich and electron-poor vinylarenes. Within a few minutes, useful chiral building blocks and intermediates can be synthesized using this practical catalytic system.

引用

页码：3133 / 3138

页数：6

共 36 条

[1] A practical, solvent free, one-pot synthesis of C2-symmetrical secondary amines [J].

Alexakis, A ;

Gille, S ;

Prian, F ;

Rosset, S ;

Ditrich, K .

TETRAHEDRON LETTERS, 2004, 45 (07) :1449-1451

[2] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[3] Modular Synthesis of Novel Chiral Phosphorous Triamides Based on (S)-N-(Pyrrolidin-2-ylmethyl)aniline and Their Application in Asymmetric Catalysis [J].

Barta, Katalin ;

Hoelscher, Markus ;

Francio, Giancarlo ;

Leitner, Walter .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (24) :4102-4116

[4]

Bogdanovic B., 1979, Adv. Organomet. Chem, V17, P105, DOI DOI 10.1016/S0065-3055(08)60322-6

[5] [(3,5-(CF3)2C6H3)4B]-[H(OET2)2]+ - A CONVENIENT REAGENT FOR GENERATION AND STABILIZATION OF CATIONIC, HIGHLY ELECTROPHILIC ORGANOMETALLIC COMPLEXES [J].

BROOKHART, M ;

GRANT, B ;

VOLPE, AF .

ORGANOMETALLICS, 1992, 11 (11) :3920-3922

[6]

BROOKHART M, 1998, Patent No. 9822424

[7] Phosphoramidite quinaphos-type ligands for highly selective Ni-catalysed asymmetric C-C bond forming reactions [J].

Diez-Holz, Christiane J. ;

Boeing, Christian ;

Francio, Giancarlo ;

Hoelscher, Markus ;

Leitner, Walter .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (18) :2995-3002

[8] Nickel catalyzed hydrovinylation of arylethylenes:: General method of synthesis of α-arylpropionic acids intermediates [J].

Fassina, V ;

Ramminger, C ;

Seferin, M ;

Monteiro, AL .

TETRAHEDRON, 2000, 56 (38) :7403-7409

[9] Weak η2-olefin bonding in palladium and platinum allyl cationic complexes containing chiral monodentate ligands with α-phenyl methyl amine side chains [J].

Filipuzzi, Serena ;

Pregosin, Paul S. ;

Calhorda, Maria Jose ;

Costa, Paulo J. .

ORGANOMETALLICS, 2008, 27 (13) :2949-2958

[10] Highly enantioselective nickel-catalyzed hydrovinylation with chiral phosphoramidite ligands [J].

Franciò, G ;

Faraone, F ;

Leitner, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :736-737

← 1 2 3 4 →