Catalyst-Controlled Chemodivergent Synthesis of Spirochromans from Diarylideneacetones and Organoboronic Acids

A chemodivergent synthesis of two series of spirochromans depending on the catalytic system was developed. Starting from diarylideneacetones and organoboronic acids, asymmetric rhodium catalysis led to the enantioselective synthesis of 4,4′-disubstituted 2,2′-spirobichromans, while acid catalysis led to the formation of 4-substituted spirochroman-2,2′-chromenes. A plausible mechanism of the chemodivergent synthesis was proposed.本研究开发了一种基于催化体系调控的两类螺色满（spirochromans）化学发散合成方法。以二芳亚甲基丙酮与有机硼酸为起始原料，通过不对称铑催化可实现4,4'-二取代-2,2'-螺双色满的对映选择性合成；而酸催化路径则可生成4-取代螺色满-2,2'-色烯。本研究同时提出了该化学发散合成的合理反应机理。