Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101 Japan.
J Org Chem. 2013 Aug 16;78(16):7903-11. doi: 10.1021/jo401072h. Epub 2013 Aug 2.
Herein, we describe the development of a method for the direct alkylation and aldol reaction of α-bromo-α-fluoro-β-lactams. This method provides facile access to a wide range of 3-alkyl- and 3-hydroxyalkyl-fluoro-β-lactams in good yields under mild conditions. The products were obtained with complete diastereoselectivity with regard to the relative configuration of the β-lactam ring at C3 and C4 positions. The reaction conditions were tolerant of a broad range of electrophiles, which highlights the overall scope and utility of this procedure.
本文描述了一种直接烷基化和α-溴-α-氟-β-内酰胺的羟醛缩合反应方法。该方法在温和条件下以良好的收率简便地获得了广泛的 3-烷基-和 3-羟烷基-氟-β-内酰胺。产物具有完全的非对映选择性，相对于 C3 和 C4 位置β-内酰胺环的相对构型。反应条件对广泛的亲电试剂具有耐受性，这突出了该方法的整体范围和实用性。
