1026995-72-1Relevant articles and documents
Ru-catalyzed asymmetric transfer hydrogenation of α-acyl butyrolactone via dynamic kinetic resolution: Asymmetric synthesis of bis-THF alcohol intermediate of darunavir
More, Ganesh V.,Malekar, Pushpa V.,Kalshetti, Rupali G.,Shinde, Mahesh H.,Ramana, Chepuri V.
, (2021/02/16)
The Ru-catalyzed enantio- and diastereoselective dynamic kinetic resolution of α-(benzyloxy/benzoyloxy)acyl-γ-butyrolactones has been examined via transfer hydrogenation. Employing the in situ prepared (R,R)-Ru-FsDPEN catalyst, the transfer hydrogenation of using formic acid/triethylamine at rt gave the corresponding (S)-3-((S)-2-(benzyloxy/benzoyloxy)-1-hydroxyethyl)dihydrofuran-2(3H)-one with good to excellent diastereo- and enantioselectivity. One of the resulting hydrogenation product prepared on gram scales was utilized for the synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3–b]furan-3-ol (1), a key synthetic intermediate of various HIV protease inhibitors such as darunavir with excellent enantio- (95% ee) and diastereoselectivities (dr 95:5).
Stereogenic: Cis -2-substituted- N -acetyl-3-hydroxy-indolines via ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation
Luo, Zhonghua,Sun, Guodong,Zhou, Zihong,Liu, Guozhu,Luan, Baolei,Lin, Yicao,Zhang, Lei,Wang, Zhongqing
supporting information, p. 13503 - 13506 (2018/12/12)
Ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation of racemic 2-substituted-N-acetyl-3-oxoindolines to cis-2-substituted-N-acetyl-3-hydroxyindolines is reported. Using the homochiral {Ru[TfDPEN](p-cymene)} catalyst with S/C = 400 in a HCO2H/Et3N mixture, up to >99.9% ee and >99:1 dr are obtained with high yields (79-98%). This method provides the first example of preparing enantiomerically pure indolines through asymmetric transfer hydrogenation (ATH).