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

作者: Angeles Gama , Lucı́a Z. Flores-López , Gerardo Aguirre , Miguel Parra-Hake , Ratnasamy Somanathan

DOI: 10.1016/S0957-4166(02)00073-3

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摘要: New chiral Schiff base ligands derived from salicylaldehydes bearing bulky ring substituents were synthesized by reaction with various amino alcohols. These new used titanium tetraisopropoxide to study steric effects on the enantioselectivity of trimethylsilylcyanation aldehydes.

参考文章(23)
Otto Meth-Cohn, Alan R. Katritzky, Charles W. Rees, Comprehensive organic functional group transformations II Pergamon , Elsevier Science. ,(1995)
Barry R. Matthews, Helen Gountzos, W.Roy Jackson, Keith G. Watson, Synthesis of threo-3-aryl-2,3-dihydroxypropanoic acid derivatives with high optical purity Tetrahedron Letters. ,vol. 30, pp. 5157- 5158 ,(1989) , 10.1016/S0040-4039(01)93473-2
Franz Effenberger, Beate Gutterer, Jürgen Jäger, Stereoselective synthesis of (1R)- and (1R,2S)-1-aryl-2-alkylamino alcohols from (R)-cyanohydrins Tetrahedron: Asymmetry. ,vol. 8, pp. 459- 467 ,(1997) , 10.1016/S0957-4166(96)00527-7
Harald Gröger, Emine Capan, Anita Barthuber, Klaus-Dieter Vorlop, Asymmetric synthesis of an (R)-cyanohydrin using enzymes entrapped in lens-shaped gels. Organic Letters. ,vol. 3, pp. 1969- 1972 ,(2001) , 10.1021/OL015920G
Jay F. Larrow, Eric N. Jacobsen, Yun Gao, Yaping Hong, Xiaoyi Nie, Charles M. Zepp, A Practical Method for the Large-Scale Preparation of [N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(III) chloride, a Highly Enantioselective Epoxidation Catalyst Journal of Organic Chemistry. ,vol. 59, pp. 1939- 1942 ,(1994) , 10.1021/JO00086A062
Yoshitaka Hamashima, Motomu Kanai, Masakatsu Shibasaki, Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning Tetrahedron Letters. ,vol. 42, pp. 691- 694 ,(2001) , 10.1016/S0040-4039(00)02039-6
Robert J. H. Gregory, Cyanohydrins in Nature and the Laboratory:  Biology, Preparations, and Synthetic Applications Chemical Reviews. ,vol. 99, pp. 3649- 3682 ,(1999) , 10.1021/CR9902906
Wei Zhang, Jennifer L. Loebach, Scott R. Wilson, Eric N. Jacobsen, Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)Manganese Complexes Journal of the American Chemical Society. ,vol. 112, pp. 2801- 2803 ,(1990) , 10.1021/JA00163A052
Franz Effenberger, Jürgen Jäger, Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 Journal of Organic Chemistry. ,vol. 62, pp. 3867- 3873 ,(1997) , 10.1021/JO970032D
Franz Effenberger, Synthesis and Reactions of Optically Active Cyanohydrins Angewandte Chemie. ,vol. 33, pp. 1555- 1564 ,(1994) , 10.1002/ANIE.199415551