131533-40-9Relevant 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.
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
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
Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones
Tiwari, Dharmendra Kumar,Shaikh, Ashif Y.,Pavase, Laxmikant S.,Gumaste, Vikas K.,Deshmukh, Abdul Rakeeb A.S.
, p. 2524 - 2534 (2007/10/03)
Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction o
Azetidin-2,3-dione synthon for stereoselective synthesis of cis- and trans-C-3-alkyl/aryl azetidin-2-ones
Tiwari, Dharmendra Kumar,Gumaste, Vikas K.,Deshmukh, Abdul Rakeeb A. S.
, p. 115 - 122 (2007/10/03)
1,4-Bis-(4-methoxyphenyl)azetidin-2,3-dione has been prepared and used as a synthon for the stereoselective synthesis of C-3-alkyl/aryl azetidin-2-ones. Some of these are well known for their cholesterol absorption inhibitor activity. A regioselective Gri
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.
