Rational design of pseudo-enantiomeric libraries of ligands based on pyranoses for application in asymmetric catalysis
作者： Vincenzo Benessere , Matteo Lega , Francesco Ruffo
DOI: 10.1016/J.JORGANCHEM.2014.01.036
关键词:
摘要: This review deals with the solution given by synthetic chemists to overcome problem of access both enantiomers a process when carbohydrates are used as ligands. Indeed, although sugars stereochemically rich compounds, and derived from one most abundant renewable material, their use in asymmetric catalysis has been limited fact that them have D-configuration. This explains concept pseudo-enantiomeric ligands, collects examples based on pyranoses, describing relevant catalysis.
elsevier.com
sci-hub.se 参考文章(35)
T. V. RajanBabu, Branko Radetich, Kamfia K. You, Timothy A. Ayers, Albert L. Casalnuovo, Joseph C. Calabrese, Electronic Effects in Asymmetric Catalysis: Structural Studies of Precatalysts and Intermediates in Rh-Catalyzed Hydrogenation of Dimethyl Itaconate and Acetamidocinnamic Acid Derivatives Using C2-Symmetric Diarylphosphinite Ligands Journal of Organic Chemistry. ,vol. 64, pp. 3429- 3447 ,(1999) , 10.1021/JO9901182
Vincenzo Benessere, Francesco Ruffo, Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis Tetrahedron-asymmetry. ,vol. 21, pp. 171- 176 ,(2010) , 10.1016/J.TETASY.2010.01.005
Hanmin Huang, Zhuo Zheng, Huilin Chen, Changmin Bai, Junwei Wang, Readily available new pyridyl alcohols derived from d-glucose as ligands for the enantioselective addition of diethylzinc to aldehydes Tetrahedron-asymmetry. ,vol. 14, pp. 1285- 1289 ,(2003) , 10.1016/S0957-4166(03)00212-X
H. Nozaki, S. Moriuti, H. Takaya, R. Noyori, Asymmetric induction in carbenoid reaction by means of a dissymmetric copper chelate Tetrahedron Letters. ,vol. 7, pp. 5239- 5244 ,(1966) , 10.1016/S0040-4039(01)89263-7
Montserrat Diéguez, Oscar Pàmies, Carmen Claver, Ligands derived from carbohydrates for asymmetric catalysis Chemical Reviews. ,vol. 104, pp. 3189- 3215 ,(2004) , 10.1021/CR0306889
W. S. Knowles, Application of organometallic catalysis to the commercial production of L-DOPA Journal of Chemical Education. ,vol. 63, pp. 222- ,(1986) , 10.1021/ED063P222
Barry M. Trost, David L. Van Vranken, Carsten Bingel, A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations Journal of the American Chemical Society. ,vol. 114, pp. 9327- 9343 ,(1992) , 10.1021/JA00050A013
T. P. Yoon, Privileged Chiral Catalysts Science. ,vol. 299, pp. 1691- 1693 ,(2003) , 10.1126/SCIENCE.1083622
T. V. RajanBabu, Timothy A. Ayers, Gary A. Halliday, Kimberly K. You, Joseph C. Calabrese, Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand Precursors Journal of Organic Chemistry. ,vol. 62, pp. 6012- 6028 ,(1997) , 10.1021/JO970884D
Hans-Ulrich Blaser, Benoît Pugin, Felix Spindler, Progress in enantioselective catalysis assessed from an industrial point of view Journal of Molecular Catalysis A: Chemical. ,vol. 231, pp. 1- 20 ,(2005) , 10.1016/J.MOLCATA.2004.11.025