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 le...

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Bibliographic Details
Published in:ACS catalysis 2020-02, Vol.10 (4), p.2596-2602
Main Authors: Liu, Na, Zhu, Wanjiang, Yao, Jian, Yin, Long, Lu, Tao, Dou, Xiaowei
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b05577