Titanium(IV) as an essential promoter in the asymmetric addition of diethylzinc to aldehydes catalyzed by aminonaphthol and imme ligands based on 3-substituted binaphthol

被引：18

作者：

Jiang, Fu-Yong ^{[1
]}

Liu, Bing ^{[1
]}

Dong, Zhi-Bing ^{[1
]}

Li, Jin-Shan ^{[1
]}

机构：

[1] Nankai Univ, State Key lab Elemento Organ Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2007年 / 692卷 / 20期

基金：

中国国家自然科学基金;

关键词：

reductive amination; BINOL; diethylzinc; titanium tetraisopropoxide;

D O I：

10.1016/j.jorganchem.2007.07.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By using indirect reductive amination and condensation, two types of aminonaphthol and imine ligands based on 3-substituted binaphthol have been synthesized, respectively. When their catalytic effectiveness was tested by the ethylation of aldehydes with diethylzinc, titanium tetraisopropoxide was found essential to get good results with ee up to 90%. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：4377 / 4380

页数：4

共 31 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
AbdelMagid, AF
Carson, KG
Harris, BD
Maryanoff, CA
Shah, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
[2] The importance of nitrogen substituents in chiral amino thiol ligands for the asymmetric addition of diethylzinc to aromatic aldehydes
Anderson, JC
Harding, M
[J]. CHEMICAL COMMUNICATIONS, 1998, (03) : 393 - 394
[3] The regioisomeric triphenylaminoethanols - Comparison of their efficiency in enantioselective catalysis
Braun, M
Fleischer, R
Mai, B
Schneider, MA
Lachenicht, S
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (04) : 474 - 482
[4] Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts
Bringmann, G
Breuning, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 667 - 679
[5] Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes
Cardellicchio, C
Ciccarella, G
Naso, F
Perna, F
Tortorella, P
[J]. TETRAHEDRON, 1999, 55 (51) : 14685 - 14692
[6] Catalysis by amino acid-derived tetracoordinate complexes: Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes
Dangel, BD
Polt, R
[J]. ORGANIC LETTERS, 2000, 2 (19) : 3003 - 3006
[7] BINOL-salen metal catalysts incorporating a bifunctional design
DiMauro, EF
Kozlowski, MC
[J]. ORGANIC LETTERS, 2001, 3 (11) : 1641 - 1644
[8] Fleischer R, 1998, SYNLETT, P1441
[9] 2-piperidino-1,1,2-triphenylethanol:: A highly effective catalyst for the enantioselective arylation of aldehydes
Fontes, M
Verdaguer, X
Solà, L
Pericàs, MA
Riera, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2532 - 2543
[10] Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines promoted by 2-azanorbornylmethanols
Guijarro, D
Pinho, P
Andersson, PG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2530 - 2535

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