Synthesis of a novel photoresponsive axially chiral phosphine ligand containing an arylazo group and its application to palladium-catalyzed asymmetric allylic alkylation

被引：22

作者：

Kawamura, M ^{[1
]}

Kiyotake, R ^{[1
]}

Kudo, K ^{[1
]}

机构：

[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan

来源：

CHIRALITY | 2002年 / 14卷 / 09期

关键词：

azo compounds; binaphthyl; palladium; phosphines; photoisomerization;

D O I：

10.1002/chir.10131

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Novel photoresponsive axially chiral monophosphine ligands containing azobenzene moiety were prepared and applied to a palladium-catalyzed allylic alkylation. The reaction of rac-1,3-diphenyl-2-propenyl acetate gave the alkylated products with up to 90% enantiomeric excess. The ligand exhibited a trans to cis photoisomerization upon irradiation with UV light. (C) 2002 Wiley-Liss,lnc.

引用

收藏

页码：724 / 726

页数：3

相关论文

共 23 条

[1] Cyclometalated complexes: A new class of highly efficient photorefractive materials [J].

Aiello, I ;

Dattilo, D ;

Ghedini, M ;

Golemme, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5598-5599

[2] Azo-containing phosphine complexes of palladium(II) and platinum(II) and their effectiveness in the Heck reaction:: crystal and molecular structure of [PdCl2{PPh2{1-(4-MeC6H4N2)-2-OC(O)Me-C10H5}]• 2EtOH [J].

Alder, MJ ;

Cross, WI ;

Flower, KR ;

Pritchard, RG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 590 (02) :123-128

[3] First synthesis and structural characterisation of a tertiary phosphine containing an azo linkage. [J].

Alder, MJ ;

Flower, KR ;

Pritchard, RG .

TETRAHEDRON LETTERS, 1998, 39 (21) :3571-3574

[4] Azo-containing tertiary phosphines: synthesis, reactivity and structural characterisation [J].

Alder, MJ ;

Cross, WI ;

Flower, KR ;

Pritchard, RG .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (15) :2563-2573

[5]

Ding KL, 1999, CHEM-EUR J, V5, P1734, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1734::AID-CHEM1734>3.3.CO

[6]

2-7

[7] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis [J].

Fache, F ;

Schulz, E ;

Tommasino, ML ;

Lemaire, M .

CHEMICAL REVIEWS, 2000, 100 (06) :2159-2231

[8] Structural investigations of C-nitrosobenzenes .1. Solution state H-1 NMR studies [J].

Fletcher, DA ;

Gowenlock, BG ;

Orrell, KG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (11) :2201-2205

[9] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].

FROST, CG ;

HOWARTH, J ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122

[10] MODIFICATION OF OPTICALLY-ACTIVE FERROCENYLPHOSPHINE LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

HAGIHARA, T ;

ITO, Y .

TETRAHEDRON LETTERS, 1986, 27 (02) :191-194