94612-33-6Relevant articles and documents
Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling
Wang, Fangyuan,Tan, Xuefeng,Wu, Ting,Zheng, Long-Sheng,Chen, Gen-Qiang,Zhang, Xumu
, p. 15557 - 15560 (2020/12/30)
Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is
A novel asymmetric synthesis of 3-(1H-pyrrol-1-yl)-substituted β-lactams via a bismuth nitrate-catalyzed reaction
Shaikh, Aarif L.,Banik, Bimal K.
scheme or table, p. 839 - 844 (2012/06/16)
The reaction of racemic α-keto β-lactams 5a-5c with the commercially available chiral compound trans-4-hydroxy-L-proline (6) in the presence of a catalytic amount of Bi(NO3)3·5 H 2O in EtOH gave a diastereoisomer mixture o
A novel one-step approach for the preparation of α-amino acids, α-amino amides, and dipeptides from azetidine-2,3-diones
Alcaide, Benito,Almendros, Pedro,Aragoncillo, Cristina
, p. 3646 - 3652 (2007/10/03)
A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of α-amino acids, α-amino amides, and dipeptides, was developed in both
