The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA.
Org Biomol Chem. 2009 Dec 7;7(23):4960-4. doi: 10.1039/b913336d. Epub 2009 Oct 6.
A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from beta-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the beta-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.
本文公开了一种方便的方法，可通过一锅芳基炔酰基-烷基化/缩合程序，由β-酮酯合成 3-羟基异喹啉和 2-羟基-1,4-萘醌。当与β-酮酯底物的一步合成方法结合使用时，该方法仅从商业上可获得的羧酸起始原料经过两步即可提供这些多环芳烃结构的新途径。该方法的实用性在对映异构 PN-配体 QUINAP 的合成中得到了证明。
