112383-87-6Relevant academic research and scientific papers
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
supporting information, 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.
, 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
Facile radical mediated synthesis of azetidin-2,3-diones: Potential synthons for biologically active compounds
Bari, Shamsher S.,Magtoof, Mehmood S.,Bhalla, Aman
experimental part, p. 987 - 991 (2011/09/21)
An operationally simple and efficient approach for the synthesis of azetidin-2,3-diones is described. The starting substrate 2-(2-bromobenzyloxy) ethanoyl chloride was treated with appropriate Schiff's bases in triethylamine and dichloromethane to afford
A β-Lactam Approach to γ-Amino-β-Keto Acid Derivatives.
Palomo, Claudio,Cossio, Fernando P.,Rubiales, Gloria,Aparicio, Domitila
, p. 3115 - 3118 (2007/10/02)
Formation of γ-amino-β-keto acid derivatives by enolate acylation with N-carboxyanhydrides previously formed from α-keto β-lactams is described.
Tributyltin Hydride Addition to Nitroalkenes: A Convenient Procedure for the Conversion of Nitroalkenes into Nitroalkanes and Carbonyl Compounds
Palomo, Claudio,Aizpurua, Jesus M.,Cossio, Fernando P.,Garcia, Jesus M.,Lopez, M. Concepcion,Oiarbide, Mikel
, p. 2070 - 2078 (2007/10/02)
A new procedure for the reduction of nitroalkenes by using n-tributyltin hydride as reducing agent is desribed.The reaction proceeds under almost neutral conditions and works well even in the presence of other reduceable functionalities.Hydrolysis and Nef reaction of the resulting nitronates furnished nitroalkanes and carbonyl compounds respectively in high yields.Application of this methodology to the preparation of β-lactam building blocks is also made.
SYNTHETIC UTILITY OF AZETIDINE-2,3-DIONES: A NEW APPROACH TO 3-HYDROXYETHYL-β-LACTAMS AND α-AMINOACID DERIVATIVES
Cossio, Fernando P.,Lopez, Concepcion,Oiarbide, Mikel,Palomo, Claudio,Aparicio, Domitila,Rubiales, Gloria
, p. 3133 - 3136 (2007/10/02)
Baeyer-Villiger oxidation of azetidine-2,3-diones provides a new route to α-aminoacid-N-carboxyanhydrides.Conversion of azetidine-2,3-diones into 3-acetyl-β-lactams is also described.
N,N-DIMETHYLPHOSPHORAMIDIC DICHLORIDE: A CONVENIENT REAGENT FOR THE PREPARATION OF β-LACTAMS FROM ACETIC ACIDS AND IMINES
Cossio, Fernando P.,Ganboa, Inaki,Garcia, Jesus M.,Lecea, Begona,Palomo, C.
, p. 1945 - 1948 (2007/10/02)
A convenient reagent for the preparation of β-lactams from acetic acids and imines is described.A new route to α-keto-β-lactams from 3-bis(ethylthio)β-lactams is also reported.Reaction of 4-acethyl-β-lactams with diazomethane is also made.
A CONVENIENT SYNTHESIS OF AZETIDINE-2,3-DIONES (α-Keto-β-Lactams)
Manhas, M. S.,Bari, S. S.,Bose, Bhawal,Bose, Ajay K.
, p. 4733 - 4736 (2007/10/02)
Azetidine-2,3-diones can be conveniently synthesized by mild hydrolisis of the product of the reaction between α-phenylthio-β-lactams and sulfuryl chloride.
