Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Synthesis of 2,2-Difluorinated 4-Isoflavanols/4-Thioisoflavanols via a Base-Catalyzed [4 + 2] Annulation Reaction of gem-Difluoroolefins

Synthesis of 2,2-Difluorinated 4-Isoflavanols/4-Thioisoflavanols via a Base-Catalyzed [4 + 2] Annulation Reaction of gem-Difluoroolefins
Mang Wang, Cong Xu, Jiaheng Li, Na Wei
DBU-catalyzed sequential intermolecular and intramolecular nucleophilic addition reactions between gem-difluoroolefins and o-hydroxy/mercapto benzaldehydes have been developed to provide a [4 + 2] annulation strategy for facile synthesis of gem-difluorinated isoflavanol derivatives. The competitive addition–elimination reaction of gem-difluoroolefins with nucleophiles was avoided under mild conditions, affording 2,2-difluorinated 4-isoflavanols or 2,2-difluoriated 4-thioisoflavanols in good to excellent yields.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01635

DOI: 10.1021/acs.joc.7b01635

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