NEW GLYCOSYL-ALPHA-AMINO-TETRAZOLE-BASED CATALYSTS FOR ALDOLISATION AND MICHAEL ADDITION

Lucie Wynands ^1,2,3 Albert Nguyen Van Nhien ^1,3 Elena Soriano ⁴ José Marco-Contelles ⁴ Denis Postel ^1,3

¹Laboratoire des Glucides - FRE3517, Université de Picardie Jules Verne, Faculté des Sciences, 33 rue Saint Leu, 80039 Amiens
²Laboratoire de Réactivité et de Chimie des Solides - UMR7314, Université de Picardie Jules Verne, Faculté des Sciences, 33 rue Saint Leu, 80039 Amiens
³Institut de Chimie de Picardie, FR3085 CNRS, 33 rue saint leu, 80039 Amiens cedex 1
⁴Laboratorio de Química Médical, (IQOG, CSIC), C/ Juan de la Cierva,3, 28006-Madrid

For the last few decades, organocatalysis has received much attention. Recently, the intrinsic chirality of carbohydrates has been used to develop new versatile catalysts ^1,2,3 in aldol, Mannich reaction,...

Those catalysts mainly present an (di)amino and a carboxylic group and can be associated to a thiourea spacer following the reaction.

Here, we report the synthesis of new glycosyl-α-aminotetrazole and their investigation as organocatalysts in aldol and (one-pot) Michael addition in heterogenous conditions using supported enzyme CAL-B.

¹Dwivedi, N.; Bischt, S. S.; Tripathi, R.P.; Carbohydr. Res., 2006, 341, 2737

²Shen, C.; Shen, F; Xia, H.; Zhang, P.; Chen, X.; Tetrahedron: Assymetry, 2011, 22, 708-712

³Singh, N.; Pandey, J.; Tripathi, R.P., 2011, 76, 3502-3505