Asymmetric reductions and C-X bond forming reactions are useful tool for preparing valuable chiral compounds. Whereas today ligands for Ru/Rh-reduction of functionalized olefins are available, the reduction of unfunctionalized olefins is by far less developed. On the other hand, new articles are continuously being published to solve the problem of using other "exotic" nucleophiles for Pd-catalyzed asymmetric allylic substitution. In addition, for both processes ligands rarely tolerate a wide range of substrates and different ligands are required for different substrates to optimize enantiopurity. Ligands with wide substrate scope and that are suitable for a large number of nucleophiles are desirable for synthesizing more complex chiral organic molecules. The discovery of "privileged ligands" easy to handle (solid, robust and air stable) and prepare from simple starting materials and good for a broad range of substrates and nucleophiles is a relevant issue. Our group has contributed in this field with an improved generation of ligands. We have shown that the introduction of phosphite groups into ligand is beneficial.[1] In this communication I will present our progress in this field. [1] See, for example: a) J. J. Verendel, O. Pàmies, M. Diéguez, P. G. Andersson, Chem. Rev. 2014, 114, 2130. b) M. Diéguez, J. Mazuela, O. Pàmies, J. J. Verendel, P. G. Andersson, J. Am. Chem. Soc. 2008, 130, 7208. c) J. Mazuela, J. J.; Verendel, M. Coll, B. Schäffner, A. Börner, P. G. Andersson, O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2009, 131, 12344. d) J. Mazuela, P.-O. Norrby, P. G. Andersson, O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2011, 133, 13634. e) M. Biosca, A. Paptchikhine, O. Pàmies, P. G. Andersson, M. Diéguez, Chem. Eur. J. 2015, 21, 3455. f) O. Pàmies, M. Diéguez, Acc. Chem. Res. 2010, 43, 212.

Theoretically-guided optimization of new ligand libraries for asymmetric reduction and C-C bond coupling reactions

251st National Meeting (2016)

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