Synthesis, Inhaltsverzeichnis Synthesis 2022; 54(10): 2433-2446DOI: 10.1055/s-0040-1719883 paper Rh2(esp)2-Catalyzed Redox/Cycloaddition Cascade of Diazoacetoacetate Enones with N-Methyl Nitrones: Diastereoselective Synthesis of β-Lactams with Two Adjacent Chiral Centers Yingjun Zhao , Rujie Xu , Zhengqing Xu , Xichen Xu ∗Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A Rh2(esp)2-catalyzed diastereoselective synthesis of highly functionalized β-lactams is developed. By employing Rh2(esp)2 as the catalyst, a reaction cascade operates by reducing an N-methyl nitrone to the corresponding N-methyl imine in the presence of a first molecule of the diazoacetoacetate enone. A second molecule of the diazoacetoacetate enone sensing a change in the reaction medium undergoes a Wolff rearrangement to afford a vinyl ketene. This vinyl ketene then reacts with the in situ generated N-methyl imine to diastereoselectively furnish a β-lactam with two contiguous stereogenic centers. Extension of this method to the [2+2]-cycloaddition of PMB-protected imines and diazoacetoacetate enones catalyzed by Rh2(esp)2 is also reported. Key words Key wordsRh2(esp)2 - diazoacetoacetate enones - N-methyl nitrones - redox - β-lactams Volltext Referenzen References 1a Liu B, Hamrick J, Daigle DM, Condon SM. Med. Chem. Rev. 2019; 54: 253 1b Shalaby MW, Dokla EM. E, Serya RA. T, Abouzid KA. M. Eur. J. Med. Chem. 2020; 199: 112312 2a Burke TP. Cell 2018; 172: 891 2b Dik DA, Fisher JF, Mobashery S. Chem. Rev. 2018; 118: 5952 2c Heffernan AJ, Sime FB, Lipman J, Roberts JA. Drugs 2018; 78: 621 2d Shirley M. Drugs 2018; 78: 675 2e Jean SS, Gould IM, Lee WS, Hsueh PR. Drugs 2019; 79: 705 2f Sonawane AD, Sonawane RA, Ninomiya M, Koketsu M. Adv. Synth. Catal. 2020; 362: 3485 2g Alves NG, Alves AJ. S, Soares MI. L, Pinho e Melo TM. V. 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