1017294-05-1Relevant articles and documents
P-Stereogenic N-Phosphine-Phosphite Ligands for the Rh-Catalyzed Hydrogenation of Olefins
Biosca, Maria,De La Cruz-Sánchez, Pol,Diéguez, Montserrat,Pàmies, Oscar
, p. 4730 - 4739 (2020/05/08)
We have identified a successful family of simple P-stereogenic N-phosphine-phosphite ligands for the Rh-catalyzed asymmetric hydrogenation of olefins. These catalysts show excellent enantiocontrol for α-dehydroamino acid derivatives and α-enamides (ee's u
Chiral rhodium complexes derived from electron-rich phosphine-phosphites as asymmetric hydrogenation catalysts
Etayo, Pablo,Nunez-Rico, Jose L.,Vidal-Ferran, Anton
experimental part, p. 6718 - 6725 (2012/02/05)
Two new chiral cationic rhodium(I) complexes derived from electron-rich dicyclohexylphosphine-phosphite ligands were prepared from enantiopure Sharpless epoxy ethers. The best-performing catalyst system, which bears a less bulky methyl ether moiety, exhibited remarkably high enantioselectivity (up to 99% ee) and reactivity (up to >2500 TON) in asymmetric hydrogenation reactions of various functionalized alkenes (α-(acylamino)acrylates, itaconic acid derivatives, α-substituted enol esters and α-arylenamides). Our synthetic methodology has been successfully applied to the enantioselective synthesis of the antiepileptic drug (R)-lacosamide (Vimpat).
Enantioselective access to chiral drugs by using asymmetric hydrogenation catalyzed by Rh(P-OP) complexes
Etayo, Pablo,Nunez-Rico, Jose Luis,Fernandez-Perez, Hector,Vidal-Ferran, Anton
supporting information; experimental part, p. 13978 - 13982 (2012/01/06)
P-OP art: Rhodium complexes of P-OP ligands serve as highly efficient and enantioselective catalysts in asymmetric hydrogenation leading to various valuable pharmaceutical building blocks and several direct precursors of chiral drugs such as LY2497282, la
Development of a pratical synthisis of DPP IV inhibitor LY2497282
Yu, Hannah,Richey, Rachel N.,Stout, James R.,LaPack, Mark A.,Gu, Ruilin,Khau, Vien V.,Frank, Scott A.,Ott, Joel P.,Miller, Richard D.,Carr, Michael A.,Zhang, Tony Y.
, p. 218 - 225 (2013/01/03)
A new synthetic route to LY2497282 (1), a potent and selective DPP IV inhibitor for the potential treatment of diabetes, suitable for the preparation of multikilogram quantities is described. The key step involved a stereoselective addition of the dianion of nicotinamide 8 to iV-dibenzyl-protected α-amino aldehyde 12, which was derived from iV-acetyl-protected amino ester 14 without epimerization. The desired Felkin-Anh nonchelation controlled anti-amino alcohol 11 was isolated with >99% HPLC area and > 99% ee by crystallization. After removing the dibenzyl protecting group under transfer hydrogenation conditions, LY2497282 (1) was finally obtained in 39% overall yield with a six-step longest linear sequence starting from N-acetyl-protected amino ester 14.