Steric effects in the design of chiral Schiff base-titanium complexes:: new catalysts for asymmetric trimethylsilylcyanation of aldehydes

被引：39

作者：

Gama, A

Flores-López, LZ

Aguirre, G

Parra-Hake, M

Somanathan, R

Walsh, PJ

机构：

[1] Inst Tecnol Tijuana, Ctr Grad & Invest, Tijuana 22000, BC, Mexico

[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(02)00073-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New chiral Schiff base ligands derived from salicylaldehydes bearing bulky ring substituents were synthesized by reaction with various amino alcohols. These new ligands were used with titanium tetraisopropoxide to study steric effects on the enantioselectivity of the trimethylsilyleyanation of aldehydes. (C) 2002 Published by Elsevier Science Ltd.

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页码：149 / 154

页数：6

相关论文

共 23 条

[1] The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex [J].

Belokon, YN ;

Green, B ;

Ikonnikov, NS ;

North, M ;

Tararov, VI .

TETRAHEDRON LETTERS, 1999, 40 (46) :8147-8150

[2] Optimized catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones [J].

Belokon, YN ;

Green, B ;

Ikonnikov, NS ;

North, M ;

Parsons, T ;

Tararov, VI .

TETRAHEDRON, 2001, 57 (04) :771-779

[3] A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst [J].

Belokon', YN ;

Davies, RG ;

North, M .

TETRAHEDRON LETTERS, 2000, 41 (37) :7245-7248

[4] Enzyme-catalyzed reactions .28. Synthesis of the adrenergic bronchodilators (R)-terbutaline and (R)-salbutamol from (R)-cyanohydrins [J].

Effenberger, F ;

Jager, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3867-3873

[5]

EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551

[6] Enzyme catalyzed reactions .26. Stereoselective synthesis of (1R)- and (1R,2S)-1-aryl-2-alkylamino alcohols from (R)-cyanohydrins [J].

Effenberger, F ;

Gutterer, B ;

Jager, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :459-467

[7] Structure/enantioselectivity study of the asymmetric addition of trimethylsilylcyanide to benzaldehyde catalyzed by Ti(IV)-Schiff base complexes [J].

Flores-Lopéz, LZ ;

Parra-Hake, M ;

Somanathan, R ;

Walsh, PJ .

ORGANOMETALLICS, 2000, 19 (11) :2153-2160

[8] Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].

Gregory, RJH .

CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682

[9] Asymmetric synthesis of an (R)-cyanohydrin using enzymes entrapped in lens-shaped gels [J].

Gröger, H ;

Capan, E ;

Barthuber, A ;

Vorlop, KD .

ORGANIC LETTERS, 2001, 3 (13) :1969-1972

[10] Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning [J].

Hamashima, Y ;

Kanai, M ;

Shibasaki, M .

TETRAHEDRON LETTERS, 2001, 42 (04) :691-694