TY - JOUR AU - Maciejko, Magdalena; Stecko, Sebastian; Staszewska-Krajewska, Olga; Jurczak, Margarita; Furman, Bartłomiej; Chmielewski, Marek TI - An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction SN - 0039-7881 SN - 1437-210X PY - 2012 JO - Synthesis JF - Synthesis LA - EN VL - 44 IS - 18 SP - 2825 EP - 2839 ET - 2012/08/13 DA - 2012/09/06 KW - β-lactams KW - Kinugasa reaction KW - carbapenem antibiotics KW - nitrones KW - acetylenes AB - The copper(I)-mediated reaction between five-membered cyclic nitrones and terminal acetylenes, leading to the assembly of the basic skeleton of carbapenem antibiotics is described. The diastereoselectivity of this cycloaddition–rearrangement cascade, a process known as the Kinugasa reaction, with respect to the structure and configuration of both substrates, as well as the reaction conditions, are discussed. Application of the described methodology to sugar-derived nitrones offers an attractive entry toward thienamycin and related compounds. PB - © Georg Thieme Verlag DO - 10.1055/s-0032-1316732 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0032-1316732 ER -