The backbone of D-glucosamine hydrochloride
was fine-tuned and modified by protecting the hydroxyl groups. In order to
reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts
were prepared and screened. Methyl-4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyr
anoside was found as the best catalyst. The reduction was proceeded under CHCl3
as solvent at 40?C, affording 68% - 94% yield.
Tripathi, R.P., Verma, S.S., Pandey, J. and Tiwari, V.K. (2008) Recent Development on Catalytic Reductive Amination and Applications. Current Organic Chemistry, 12, 1093-1115. http://dx.doi.org/10.2174/138527208785740283
Connolly, T.J., Constantinescu, A., Lane, T.S., Matchett, M., Mcgarry, P. and Paperna, M. (2005) Assessment of a Reductive Amination Route to Methyl(3-nitrobenzyl)amine Hydrochloride. Organic Process Research & Development, 9, 837-842. http://dx.doi.org/10.1021/op050120x
Heydari, A., Khaksar, S., Akbari, J., Esfandyari, M., Pourayoubi, M. and Tajbakhsh, M. (2007) Direct Reductive Amination and Selective 1,2-Reduction of alpha,beta-Unsaturated Aldehydes and Ketones by NaBH4 Using H3PW12O40 as Catalyst. Tetrahedron Letters, 48, 1135-1138. http://dx.doi.org/10.1016/j.tetlet.2006.12.069
Becker, C., Hoben, C. and Kunz, H. (2007) Enantioselective Organocatalysis of Strecker and Mannich Reactions Based on Carbohydrates. Advanced Synthesis & Catalysis, 349, 417-424. http://dx.doi.org/10.1002/adsc.200600370
Liu, K., Cui, H.F., Nie, J., Dong, K.Y., Li, X.J. and Ma, J.A. (2007) Highly Enantioselective Michael Addition of Aromatic Ketones to Nitroolefins Promoted by Chiral Bifunctional Primary Amine-Thiourea Catalysts Based on Saccharides. Organic Letters, 9, 923-925. http://dx.doi.org/10.1021/ol0701666
Dekamin, M.G., Azimoshan, M. and Ramezani, L. (2013) Chitosan: A Highly Efficient Renewable and Recoverable Bio-Polymer Catalyst for the Expeditious Synthesis of Alpha-Amino Nitriles and Imines under Mild Conditions. Green Chemistry, 15, 811-820. http://dx.doi.org/10.1039/c3gc36901c
Shen, C., Shen, F.Y., Xia, H.J., Zhang, P.F. and Chen, X.Z. (2011) Carbohydrate-Derived Alcohols as Organocatalysts in Enantioselective Aldol Reactions of Isatins with Ketones. Tetrahedron: Asymmetry, 22, 708-712.
Shen, C., Shen, F., Zhou, G., Xia, H., Chen, X., Liu, X. and Zhang, P. (2012) Novel Carbohydrate-Derived Prolinamide as a Highly Efficient, Recoverable Catalyst for Direct Aldol Reactions in Water. Catalysis Communications, 26, 6-10.
Ji, L., Zhang, D.F., Zhao, Q., Hu, S.M., Qian, C. and Chen, X.Z. (2013) Diastereospecific Epoxidation and Highly Regioselective Ring-Opening of (+)-Valienamine: Practical Synthesis of (+)-Valiolamine. Tetrahedron, 69, 7031-7037.
Xia, H.J., Yan, H., Shen, C., Shen, F.Y. and Zhang, P.F. (2011) Syn-thesis of Novel Carbohydrate-Based Chiral P, N Ligands and Their Applications in Cu-Catalyzed Enantioselective 1, 4-Conjugate Additions. Catalysis Communications, 16, 155-158. http://dx.doi.org/10.1016/j.catcom.2011.09.021
Ji, L., Zhou, G.Q., Qian, C. and Chen, X.Z. (2014) Synthesis of 1,2,3-Triazoles from Azide-Derivatised Aminocyclitols by Catalytic Diazo Transfer and CuAAC Click Chemistry. European Journal of Organic Chemistry, 2014, 3622- 3636. http://dx.doi.org/10.1002/ejoc.201301874
Ge, X., Qian, C. and Chen, X.Z. (2014) Synthesis of Novel Carbohydrate-Based Valine-Derived Formamide Organocatalysts by CuAAC Click Chemistry and Their Application in Asymmetric Reduction of Imines with Trichlorosilane. Tetrahedron: Asymmetry, 25, 1450-1455. http://dx.doi.org/10.1016/j.tetasy.2014.10.003