1093633-96-5Relevant academic research and scientific papers
Temperature-controlled bidirectional enantioselectivity in a dynamic catalyst for asymmetric hydrogenation
Storch, Golo,Trapp, Oliver
, p. 3580 - 3586 (2015)
Asymmetric catalysis using enantiomerically pure catalysts is one of the most widely used methods for the preparation of enantiomerically pure compounds. The separate synthesis of both enantiomerically pure compounds requires tedious and time-consuming pr
Temperature-Controlled Bidirectional Enantioselectivity in Asymmetric Hydrogenation Reactions Utilizing Stereodynamic Iridium Complexes
Siebert, Max,Storch, Golo,Rominger, Frank,Trapp, Oliver
, p. 3485 - 3494 (2017)
Stereochemically flexible 2,2(-bis(diphenylphosphino)biphenyl (BIPHEP) ligands were modified with chiral α-substituted carboxylic acid auxiliaries in the 3- and 3′-position. The resulting central-to-axial chirality transfer to the stereochemically flexible chiral axis of the BIPHEP core was investigated as well as complexation of these diastereomeric ligands to iridium(I). Solid-state structures of both ligand diastereomers and a diastereomerically pure iridium(I) BIPHEP complex were obtained. Thermal equilibration of the resulting iridium(I) complexes was studied to investigate the stereodynamic properties of the BIPHEP ligands. The iridium(I) complexes without and after pre-catalysis warming in solution - which induces a shift of the diastereomeric ratio - were applied for asymmetric hydrogenation of a prochiral α-substituted acrylic acid, resulting in temperature-controlled bidirectional enantioselectivity of iridium catalysts for the first time. In both cases, enantioenriched (R)-naproxen as well as (S)-naproxen - after re-equilibration of the catalyst at elevated temperatures - was obtained by using the same catalyst.
Enantiomerically pure bicyclo[3.3.1]nona-2,6-diene as the sole source of enantioselectivity in BIPHEP-Rh asymmetric hydrogenation
Punniyamurthy, Tharmalingam,Mayr, Monika,Dorofeev, Alexander S.Z.,Bataille, Carole J. R.,Gosiewska, Silvia,Nguyen, Bao,Cowley, Andrew R.,Brown, John M.
supporting information; experimental part, p. 5092 - 5094 (2009/03/11)
In situ resolution of the rapidly racemising diphosphine BIPHEP and its relatives with the cationic Rh complex of (S,S)-bicyclonona-2,6-diene permits the asymmetric hydrogenation of dehydroamino esters. The Royal Society of Chemistry.
