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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Published inACS catalysis Vol. 10; no. 4; pp. 2596 - 2602
Main Authors Liu, Na, Zhu, Wanjiang, Yao, Jian, Yin, Long, Lu, Tao, Dou, Xiaowei
Format Journal Article
LanguageEnglish
Published American Chemical Society 21.02.2020
Subjects
acid catalysis
spiroketal
chroman
chemodivergent synthesis
rhodium catalysis
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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