Small Bite-Angle P-OP Ligands for Asymmetric Hydroformylation and Hydrogenation

被引：43

作者：

Fernandez-Perez, Hector ^{[1
]}

Benet-Buchholz, J. ^{[1
]}

Vidal-Ferran, Anton ^{[1
,2
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 14期

关键词：

PHOSPHITE LIGANDS; ENANTIOSELECTIVE HYDROFORMYLATION; RHODIUM COMPLEXES;

D O I：

10.1021/ol401494x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of small bite-angle phosphine-phosphite (P-OP) ligands have been synthesized by a two-step method. The key intermediate was prepared by an unprecedented asymmetric carbonyl reduction of a phosphamide using the CBS (Corey-Bakshi-Shibata) catalyst. The topology of these ligands (a configurationally stable stereogenic carbon with two heteroatom substituents) and their small bite-angle (created by the close proximity of the two ligating groups to the metal center) together provide a rigid asymmetric environment around this center, enabling high stereoselectivity in hydroformylations and hydrogenations of standard substrates.

引用

页码：3634 / 3637

页数：4

共 25 条

[11] Chiral Rhodium Complexes Derived From Electron-Rich Phosphine-Phosphites as Asymmetric Hydrogenation Catalysts [J].

Etayo, Pablo ;

Nunez-Rico, Jose L. ;

Vidal-Ferran, Anton .

ORGANOMETALLICS, 2011, 30 (24) :6718-6725

[12] Enantioselective Access to Chiral Drugs by using Asymmetric Hydrogenation Catalyzed by Rh(P-OP) Complexes [J].

Etayo, Pablo ;

Luis Nunez-Rico, Jose ;

Fernandez-Perez, Hector ;

Vidal-Ferran, Anton .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) :13978-13982

[13] Phosphine-phosphite ligands: chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation [J].

Farkas, Gergely ;

Balogh, Szabolcs ;

Madarasz, Jozsef ;

Szollosy, Aron ;

Darvas, Ferenc ;

Urge, Laszlo ;

Gouygou, Maryse ;

Bakos, Jozsef .

DALTON TRANSACTIONS, 2012, 41 (31) :9493-9502

[14] Highly modular P-O-P ligands for asymmetric hydrogenation [J].

Fernandez-Perez, Hector ;

Pericas, Miquel A. ;

Vidal-Ferran, Anton .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :1984-1990

[15] Phosphine-Phosphinite and Phosphine-Phosphite Ligands: Preparation and Applications in Asymmetric Catalysis [J].

Fernandez-Perez, Hector ;

Etayo, Pablo ;

Panossian, Armen ;

Vidal-Ferran, Anton .

CHEMICAL REVIEWS, 2011, 111 (03) :2119-2176

[16]

Fernández-Pérez H, 2010, CHIM OGGI, V28, pXXVI

[17] Highly Modular P-OP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism [J].

Fernandez-Perez, Hector ;

Donald, Steven M. A. ;

Munslow, Ian J. ;

Benet-Buchholz, Jordi ;

Maseras, Feliu ;

Vidal-Ferran, Anton .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (22) :6495-6508

[18] Applied Hydroformylation [J].

Franke, Robert ;

Selent, Detlef ;

Boerner, Armin .

CHEMICAL REVIEWS, 2012, 112 (11) :5675-5732

[19]

Jacobsen E.N., 1999, COMPREHENSIVE ASYMME, V3

[20] [Ir(P-OP)]-Catalyzed Asymmetric Hydrogenation of Diversely Substituted C=N-Containing Heterocycles [J].

Luis Nunez-Rico, Jose ;

Vidal-Ferran, Anton .

ORGANIC LETTERS, 2013, 15 (08) :2066-2069

← 1 2 3 →