194234-97-4Relevant 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
Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach
Piens, Nicola,Goossens, Hannelore,Hertsen, Dietmar,Deketelaere, Sari,Crul, Lieselotte,Demeurisse, Lotte,De Moor, Jelle,Van den Broeck, Elias,Mollet, Karen,Van Hecke, Kristof,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 18002 - 18009 (2017/12/13)
The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr
Process for preparation of enantiomerically pure S-(+)-N, N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine
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, (2014/07/09)
The present invention relates to improved, efficient process for the preparation of enantiomerically pure S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine and pharmaceutically acid addition salts thereof. The present invention particularly provides a process for preparation of (3S, 4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one useful as a key intermediate for preparation of (s)-dapoxetine.