Mg-promoted mixed pinacol coupling

被引：50

作者：

Maekawa, H ^{[1
]}

Yamamoto, Y ^{[1
]}

Shimada, H ^{[1
]}

Yonemura, K ^{[1
]}

Nishiguchi, I ^{[1
]}

机构：

[1] Nagaoka Univ Technol, Dept Chem, Niigata 9402188, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 20期

关键词：

carbonyl compounds; electron transfer; magnesium and; compounds; coupling reaction;

D O I：

10.1016/j.tetlet.2004.03.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mg-promoted reduction of a mixture of aromatic ketones (or imines) and aliphatic carbonyl compounds in N,N-di-methylformamide (DMF) brought about unique mixed pinacol type of cross coupling to give unsymmetrical vicinal diols (or amino alcohols) or alpha-hydroxyketones in good to moderate yields. The reaction may be initiated by electron transfer from magnesium metal to an aromatic carbonyl compound possessing a less negative reduction potential. The difference of reduction potential between aromatic ketones (or imines) and aliphatic carbonyl compounds was found to be one of the important key factors in this selective cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3869 / 3872

页数：4

共 23 条

[1]

BLOOMFIELD JJ, 1976, ORGANIC REACTIONS, V23

[2] NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].

COREY, EJ ;

DANHEISER, RL ;

CHANDRASEKARAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265

[3] A SIMPLE AND EFFICIENT NEW SYNTHESIS OF VICINAL DIOLS BY REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS [J].

CSUK, R ;

FURSTNER, A ;

WEIDMANN, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (24) :1802-1803

[4] 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

[5] New developments in the chemistry of low-valent titanium [J].

Furstner, A ;

Bogdanovic, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21) :2442-2469

[6] Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines in the presence of chlorosilane and zinc metal [J].

Hatano, B ;

Ogawa, A ;

Hirao, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9421-9424

[7] Highly diastereoselective pinacol coupling of secondary aliphatic aldehydes induced by a catalytic system consisting of vanadium complex, chlorosilane, and zinc metal [J].

Hirao, T ;

Asahara, M ;

Muguruma, Y ;

Ogawa, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2812-2813

[8]

Hirao T, 1999, SYNLETT, P175

[9] STEREOSELECTIVITY IN REDUCTION OF ALIPHATIC ALPHA-KETOLS WITH ALUMINUM-HYDRIDE REAGENTS [J].

KATZENEL.JA ;

BOWLUS, SB .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (04) :627-632

[10] THE APPLICATION OF LOW-VALENT TITANIUM REAGENTS IN ORGANIC-SYNTHESIS [J].

LENOIR, D .

SYNTHESIS-STUTTGART, 1989, (12) :883-897

← 1 2 3 →