Chelating diamide based rate enhancement of intramolecular alkene hydroaminations catalyzed by a neutral Sc(III) complex

被引：106

作者：

Kim, JY ^{[1
]}

Livinghouse, T ^{[1
]}

机构：

[1] Montana State Univ, Dept Chem, Bozeman, MT 59717 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 20期

关键词：

D O I：

10.1021/ol051574h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graph Neutral scandium amido complexes are viable catalysts for intramolecular alkene hydroamination. Catalytic activity is strongly coupled to the electronic character of the ScIII(Ill) ligand environment with chelating diamide coordination providing a precatalyst possessing substantially improved activity and superb distereoselectivity in the synthesis of trans-2,5-disubstituted pyrrolidines.

引用

收藏

页码：4391 / 4393

页数：3

相关论文

共 27 条

[1] Organolanthanide-catalyzed hydroamination/cyclization. Efficient allene-based transformations for the syntheses of naturally occurring alkaloids [J].

Arredondo, VM ;

Tian, S ;

McDonald, FE ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3633-3639

[2] Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst [J].

Bexrud, JA ;

Beard, JD ;

Leitch, DC ;

Schafer, LL .

ORGANIC LETTERS, 2005, 7 (10) :1959-1962

[3] LOW COORDINATION NUMBERS IN LANTHANIDE AND ACTINIDE COMPOUNDS .1. PREPARATION AND CHARACTERIZATION OF TRIS[BIS(TRIMETHYLSILYL)-AMIDO]LANTHANIDES [J].

BRADLEY, DC ;

GHOTRA, JS ;

HART, FA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1973, (10) :1021-1027

[4] RATIONAL DESIGN IN HOMOGENEOUS CATALYSIS - IR(I)-CATALYZED ADDITION OF ANILINE TO NORBORNYLENE VIA N-H ACTIVATION [J].

CASALNUOVO, AL ;

CALABRESE, JC ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6738-6744

[5] Calcium-mediated intramolecular hydroamination catalysis [J].

Crimmin, MR ;

Casely, IJ ;

Hill, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2042-2043

[6] The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].

Dorta, R ;

Egli, P ;

Zurcher, F ;

Togni, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858

[7] ORGANOLANTHANIDE-CATALYZED HYDROAMINATION - A KINETIC, MECHANISTIC, AND DIASTEREOSELECTIVITY STUDY OF THE CYCLIZATION OF N-UNPROTECTED AMINO OLEFINS [J].

GAGNE, MR ;

STERN, CL ;

MARKS, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :275-294

[8] Hydroamination/cyclization of aminoalkenes using cationic zirconocene and titanocene catalysts [J].

Gribkov, DV ;

Hultzsch, KC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (41) :5542-5546

[9] Synthesis and characterization of new biphenolate and binaphtholate rare-earth-metal amido complexes: Catalysts for asymmetric olefin hydroamination/cyclization [J].

Gribkov, DV ;

Hultzsch, KC ;

Hampell, F .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4796-4810

[10]

GRIBKOV DV, 2004, ORGANOMETALLICS, V23, P2601