Unsymmetrical terdentate phosphorus-nitrogen-nitrogen (PNN) ligands: effect of the M/L ratio and the pendant group on stereoselectivity

被引：10

作者：

Cheng, XH ^{[1
]}

Hii, KK ^{[1
]}

机构：

[1] Kings Coll London, Dept Chem, Strand, London WC2R 2LS, England

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(03)00361-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Twelve novel, unsymmetrical terdentate pyrrolidine-based phosphorus-nitrogen ligands were prepared. These ligands promoted very high catalytic activity in the palladium-catalysed allylic substitution reactions of 1,3-diphenylpropenyl acetate with malonate esters (100% conversion at 0degreesC in <2 h). Enantioselectivities up to 94% were attained. An unusual effect of metal-to-ligand ratio was observed. Various structural features affecting the enantioselectivity and stereoinduction were examined and discussed. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：2045 / 2052

页数：8

共 13 条

[1] The first tridentate phosphine ligand combining planar, phosphorus and carbon chirality [J].

Barbaro, P ;

Bianchini, C ;

Giambastiani, G ;

Togni, A .

CHEMICAL COMMUNICATIONS, 2002, (22) :2672-2673

[2] Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins [J].

Fadini, L ;

Togni, A .

CHEMICAL COMMUNICATIONS, 2003, (01) :30-31

[3] CHIRAL (BETA-AMINOALKYL)PHOSPHINES - HIGHLY EFFICIENT PHOSPHINE-LIGANDS FOR CATALYTIC ASYMMETRIC GRIGNARD CROSS-COUPLING [J].

HAYASHI, T ;

KONISHI, M ;

FUKUSHIMA, M ;

KANEHIRA, K ;

HIOKI, T ;

KUMADA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) :2195-2202

[4] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].

Helmchen, G ;

Pfaltz, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345

[5] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands [J].

Helmchen, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :203-214

[6] Syntheses and properties of palladium complexes containing phosphorus-nitrogen-phosphorus ligands with a tunable hemilabile site [J].

Hii, KKM ;

Thornton-Pett, M ;

Jutand, A ;

Tooze, RP .

ORGANOMETALLICS, 1999, 18 (10) :1887-1896

[7] (S)-Proline-derived new chiral ligands with phosphino, organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating element [J].

Hiroi, K ;

Suzuki, Y ;

Abe, I .

TETRAHEDRON-ASYMMETRY, 1999, 10 (06) :1173-1188

[8] New, optically active phosphine oxazoline (JM-Phos) ligands: Syntheses and applications in allylation reactions [J].

Hou, DR ;

Reibenspies, JH ;

Burgess, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :206-215

[9] Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds [J].

Kanai, M ;

Nakagawa, Y ;

Tomioka, K .

TETRAHEDRON, 1999, 55 (13) :3843-3854

[10] Rhodium complexes with chiral aminophosphinite derivatives of ephedrine [J].

Kuznetsov, VF ;

Facey, GA ;

Yap, GPA ;

Alper, H .

ORGANOMETALLICS, 1999, 18 (23) :4706-4711

← 1 2 →