Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines in the presence of chlorosilane and zinc metal

被引：78

作者：

Hatano, B ^{[1
]}

Ogawa, A ^{[1
]}

Hirao, T ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 25期

关键词：

D O I：

10.1021/jo981396o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic reductive coupling of aldimines was achieved by using a catalyst Cp(2)VCl(2)/PhMe(2)SiCl/Zn system. The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the coupling products was investigated in detail. As a result, the present Cp(2)VCl(2)-catalyzed reductive coupling of aldimines in the presence of PhMe(2)SiCl and zinc metal provided the corresponding 1,2-diamines in good yield with high meso selectivity (up to 92% meso), while the reductive coupling of aldehydes, ketones, and aldimines by the hitherto known catalytic methods leads to the preferential formation of dl isomers of the coupling products.

引用

页码：9421 / 9424

页数：4

共 42 条

[1] Diastereoselective synthesis of 1,2-diphenyl-1,2-diaminoethanes by Yb(OTf)3 accelerated reductive coupling of imines [J].

Annunziata, R ;

Benaglia, M ;

Cinquini, M ;

Cozzi, F ;

Raimondi, L .

TETRAHEDRON LETTERS, 1998, 39 (20) :3333-3336

[2] SYNTHESIS OF VICINAL DIAMINES BY SMI2-PROMOTED REDUCTION OF N-(N',N'-DIALKYLAMINOALKYL)BENZOTRIAZOLES [J].

AURRECOECHEA, JM ;

FERNANDEZACEBES, A .

TETRAHEDRON LETTERS, 1992, 33 (33) :4763-4766

[3]

BARUAB B, 1995, TETRAHEDRON LETT, V36, P747

[4] REDUCTIVE DIMERIZATION OF DIFUNCTIONAL ARY IMINES ON PHOTOLYSIS [J].

BEAK, P ;

PAYET, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3281-&

[5]

BETSCHART C, 1988, HELV CHIM ACTA, V71, P19999

[6] A ROUTE TO VICINAL DIAMINES FROM THE SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ALDIMINES [J].

ENHOLM, EJ ;

FORBES, DC ;

HOLUB, DP .

SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :981-987

[7] INTERMOLECULAR PINACOL CROSS COUPLING OF ELECTRONICALLY SIMILAR ALDEHYDES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 1,2-DIOLS EMPLOYING A PRACTICAL VANADIUM(II) REAGENT [J].

FREUDENBERGER, JH ;

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8014-8016

[8] A multicomponent redox system accounts for the first Nozaki-Hiyama-Kishi reactions catalytic in chromium [J].

Furstner, A ;

Shi, NY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2533-2534

[9]

FURSTNER A, 1995, J AM CHEM SOC, V117, P4468

[10] Nozaki-Hiyama-Kishi reactions catalytic in chromium [J].

Furstner, A ;

Shi, NY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12349-12357

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