Enantioselective hydroamination/cyclization catalyzed by organolanthanide amide's derived from a new chiral ligand, (S)-2-(pyrrol-2-ylmethyleneamino)-2′-(dimethylamino)-1,1′-binaphthyl

被引：88

作者：

Zi, Guofu ^{[1
]}

Xiang, Li ^{[1
]}

Song, Haibin ^{[2
]}

机构：

[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China

[2] Nankai Univ, Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANOMETALLICS | 2008年 / 27卷 / 06期

关键词：

D O I：

10.1021/om701058k

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new series of bis-ligated organolanthanide amides, (1)2-LnN(SiMe3)(2)center dot C7H8 (Ln = Sm (2), Y (3), Yb (4)), have been prepared by the reaction of Ln[N(SiMe3)(2)](3) with the ligand (S)-2-(pyrrol-2-ylmethyleneamino)-2'-(dimethylamino)-1,1'-binaphthyl (1H) in good yields. They are active catalysts for the asymmetric hydroamination/cyclization reaction of aminoalkenes, affording cyclic amines in moderate to good conversions with moderate to good ee values.

引用

页码：1242 / 1246

页数：5

共 72 条

[1] New chiral lanthanide amide ate complexes for the catalysed synthesis of scalemic nitrogen-containing heterocycles [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Duhayon, Carine ;

Guillot, Regis ;

Lyubov, Dmitrii ;

Schulz, Emmanuelle ;

Trifonov, Alexander .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) :2189-2200

[2] New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination [J].

Aillaud, Isabelle ;

Wright, Karen ;

Collin, Jacqueline ;

Schulz, Emmanuelle ;

Mazaleyrat, Jean-Paul .

TETRAHEDRON-ASYMMETRY, 2008, 19 (01) :82-92

[3] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].

Aillaud, Isabelle ;

Collin, Jacqueline ;

Hannedouche, Jerome ;

Schulz, Emmanuelle .

DALTON TRANSACTIONS, 2007, (44) :5105-5118

[4] 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

[5] Tris(bis(trimethylsilyl)amido)samarium: X-ray structure and DFT study [J].

Brady, ED ;

Clark, DL ;

Gordon, JC ;

Hay, PJ ;

Keogh, DW ;

Poli, R ;

Scott, BL ;

Watkin, JG .

INORGANIC CHEMISTRY, 2003, 42 (21) :6682-6690

[6]

Breuzard JAJ, 2005, TOP ORGANOMETAL CHEM, V15, P231

[7]

Bytschkov I, 2003, EUR J ORG CHEM, V2003, P935

[8] Metal complexes of chiral binaphthyl Schiff-base ligands and their application in stereoselective organic transformations [J].

Che, CM ;

Huang, JS .

COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) :97-113

[9] Lanthanide complexes coordinated by N-substituted (R)-1,1′-binaphthyl-2,2′-diamido ligands in the catalysis of enantioselective intramolecular hydroamination [J].

Collin, J ;

Daran, JC ;

Jacquet, O ;

Schulz, E ;

Trifonov, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (11) :3455-3462

[10] Lanthanide complexes derived from (R)-1,1′-binaphthyl-2,2′-bis(neopentylamine) -: {Li(THF)4}{Ln[(R)-C20H12N2(C10H22)]2} (Ln = Sm, Yb) -: novel catalysts for enantioselective intramolecular hydroamination [J].

Collin, J ;

Daran, JC ;

Schulz, E ;

Trifonov, A .

CHEMICAL COMMUNICATIONS, 2003, (24) :3048-3049

← 1 2 3 4 5 6 7 8 →