Improved synthesis and crystal structure of TiCl3(tmeda)(thf):: A highly stereoselective pinacol coupling reagent for aromatic aldehydes

被引：14

作者：

Oshiki, T ^{[1
]}

Kiriyama, T ^{[1
]}

Tsuchida, K ^{[1
]}

Takai, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

CHEMISTRY LETTERS | 2000年 / 04期

关键词：

D O I：

10.1246/cl.2000.334

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A monomeric titanium(III) complex, TiCl3(tmeda)(thf) (1), has been prepared by a reaction of TICl4 with TMEDA, Zn, and a catalytic amount of PbCl2 in an almost quantitative yield. The solid state structure of 1 is revealed by X-ray crystallographic analysis. The complex 1 couples aromatic aldehydes under mild conditions to give 1,2-diols in good to excellent yields with high dl-selectivities.

引用

页码：334 / 335

页数：2

共 33 条

[1] Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium Schiff base complexes
Bandini, M
Cozzi, PG
Morganti, S
Umani-Ronchi, A
[J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 1997 - 2000
[2] Stereoselective pinacol coupling in aqueous media
Barden, MC
Schwartz, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) : 5484 - 5485
[3] COMPLEXES OF TITANIUM TRICHLORIDE
CLARK, RJH
MACHIN, DJ
LEWIS, J
NYHOLM, RS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (JAN): : 379 - &
[4] PINACOLIC COUPLING OF AROMATIC-ALDEHYDES AND KETONES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE IN BASIC-MEDIA
CLERICI, A
PORTA, O
[J]. TETRAHEDRON LETTERS, 1982, 23 (34) : 3517 - 3520
[5] A highly dl-stereoselective pinacolization of aromatic aldehydes mediated by titanium trichloride in dichloromethane
Clerici, A
Clerici, L
Porta, O
[J]. TETRAHEDRON LETTERS, 1996, 37 (17) : 3035 - 3038
[6] NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES
COREY, EJ
DANHEISER, RL
CHANDRASEKARAN, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) : 260 - 265
[7] NOVEL TITANIUM(II) AMINE COMPLEXES L4TICL2[L = 1/2 N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE (TMEDA), 1/2 N,N,N'-TRIMETHYLETHYLENEDIAMINE, PYRIDINE, 1/2 2,2'-BIPYRIDINE] - SYNTHESIS AND CRYSTAL-STRUCTURE OF MONOMERIC TRANS-(TMEDA)2TICL2
EDEMA, JJH
DUCHATEAU, R
GAMBAROTTA, S
HYNES, R
GABE, E
[J]. INORGANIC CHEMISTRY, 1991, 30 (02) : 154 - 156
[8] CARBON-CARBON BOND FORMATION BY REDUCTIVE COUPLING WITH TITANIUM(II) CHLORIDE BIS(TETRAHYDROFURAN)
EISCH, JJ
SHI, X
LASOTA, J
[J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1995, 50 (03): : 342 - 350
[9] A new look at the McMurry reaction
Ephritikhine, M
[J]. CHEMICAL COMMUNICATIONS, 1998, (23) : 2549 - 2554
[10] New developments in the chemistry of low-valent titanium
Furstner, A
Bogdanovic, B
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21): : 2442 - 2469

← 1 2 3 4 →