The development of transition metal catalyzed asymmetric hydrogenation could be stated as the cradle of modern enantioselective catalysis. Since the early asymmetric hydrogenation example from Knowles and Sabacky in 1968, the method has been rapidly advanced over the years into an important tool in academia and chemical industry.1 The pioneering work of Stephan and co-workers in 2006 extended the field of homogenous hydrogenation to the possibility of metal-free hydrogen activation based on the utilization of Frustrated Lewis pairs (FLPs).2,3 Subsequently, the concept could be applied in asymmetric catalysis and the first examples of highly enantioselective hydrogenation and hydrosilylation reactions with chiral FLPs were developed .4,5,6,7Herein, we report the application of novel chiral FLP catalysts in enantioselctive hydroboration reactions. Based on detailed mechanistic studies an enantiomeric excess up to 80% could be obtained in this challenging transformation with tailored FLP catalysts.8 References(1) Knowles, W. S.; and Sabacky, M. J.; Chem. Commun., 1968 , 1445.(2) Welch, G. C.; San Juan, R. R.; Masuda, J. D.; and Stephan, D. W.; Science, 2006  , 314, 1124.(3) Stephan, D. W.; Erker,G.; Angew. Chem. Int. Ed., 2010  , 49, 46.(4) Chen, D.; Klankermayer, J.; Chem. Commun., 2008 , 2130;(5) Chen, D.; Wang, Y.; Klankermayer, J. Angew. Chem. Int. Ed., 2010  , 49, 9475.(6) Ghattas, G.; Chen, D.; Pan, F.; Klankermayer, J. Dalton Trans., 2012  , 41, 9026.(7) Chen, D.; Leich, V.; Pan, F.; Klankermayer, J. Chem. Eur. J.,2012  , 18, 5184(8) Ghattas, G.; Chen, D.; Klankermayer, J. manuscript to be submitted.

Enantioselective hydroboration with chiral frustrated Lewis pairs

248th National Meeting (2014)

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