Catalyst-Controlled Chemodivergent Synthesis of Spirochromans from Diarylideneacetones and Organoboronic Acids
Na Liu, Wanjiang Zhu, Jian Yao, Long Yin, Tao Lu, Xiaowei Dou
Abstract
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.
Topics & Concepts
Enantioselective synthesisCatalysisRhodiumChemistryCombinatorial chemistryOrganic chemistrySynthesis of Indole DerivativesOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods