Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium Schiff base complexes

被引：68

作者：

Bandini, M ^{[1
]}

Cozzi, PG ^{[1
]}

Morganti, S ^{[1
]}

Umani-Ronchi, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(99)00100-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)(2) and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1997 / 2000

页数：4

共 13 条

[1] Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides [J].

Cole, BM ;

Shimizu, KD ;

Krueger, CA ;

Harrity, JPA ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1668-1671

[2] Halide titanium(IV) Schiff base complexes; fluoride and bromide derivatives and evidence for a new seven-coordinate chloride intermediate [J].

Coles, SJ ;

Hursthouse, MB ;

Kelly, DG ;

Toner, AJ ;

Walker, NM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (20) :3489-3494

[3]

Fleischer R, 1998, EUR J ORG CHEM, V1998, P1063

[4] Combinatorial approach to the discovery of novel coordination complexes [J].

Francis, MB ;

Finney, NS ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8983-8984

[5] CHEMISTRY OF AND WITH HIGHLY REACTIVE METALS [J].

FURSTNER, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) :164-189

[6]

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

[7]

Gansauer A, 1997, SYNLETT, P363

[8] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES CATALYZED BY CHIRAL SCHIFF-BASE TITANIUM ALKOXIDE COMPLEXES [J].

HAYASHI, M ;

MIYAMOTO, Y ;

INOUE, T ;

OGUNI, N .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1515-1522

[9] A novel catalytic system for one-electron reduction. Low valent vanadium-catalyzed coupling of aldehydes [J].

Hirao, T ;

Hasegawa, T ;

Muguruma, Y ;

Ikeda, I .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :366-367

[10] Asymmetric synthesis .27. Asymmetric catalytic trimethylsilylcyanation of aldehydes by novel Ti-chiral Schiff base complexes [J].

Jiang, YZ ;

Zhou, XG ;

Hu, WH ;

Li, Z ;

Mi, AQ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2915-2916

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