Enantiodivergent asymmetric catalysis with the tropos BIPHEP ligand and a proline derivative as chiral selector.

ABSTRACT: A catalytic system based on the tropos ligand BIPHEP and (S)-proline methyl ester as chiral selector was studied for Rh-catalysed asymmetric catalysis. By careful control of the catalyst preformation conditions, the enantioselectivity could be completely reversed in asymmetric hydrogenation of prochiral olefins maintaining the same absolute level in favorable cases. The enantiodivergent asymmetric catalysis could be rationalised by the interplay of the dynamic chirality (tropos) of the phosphine ligand and the coordination of the proline selector. Treating a suitable Rh-BIPHEP precursor with the (S_c)-proline-based ionic liquid led to an equimolar mixture of (R_aS_c)- and (S_aS_c)-dias

SUBMITTER: Oczipka P 

PROVIDER: S-EPMC5952544 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature