Triethylamine-Promoted Henry Reaction/Elimination of HNO 2 /Cyclization Sequence of Functionalized Nitroalkanes and 2-Oxoaldehydes: Diversity-Oriented Synthesis of Oxacycles

The triethylamine-promoted cascade Henry reaction/elimination of HNO /cyclization reaction of 2-oxoaldehydes with nitroalkanes bearing various remote functionalities is described. Both chiral and achiral nitroalkanes were applicable to this protocol, leading to a variety of oxacycles, such as chrome...

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Published inOrganic letters Vol. 25; no. 22; pp. 4033 - 4037
Main Authors Lu, Yu-Xia, Lv, Xue-Jiao, Liu, Chang, Liu, Yan-Kai
Format Journal Article
LanguageEnglish
Published United States 09.06.2023
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Summary:The triethylamine-promoted cascade Henry reaction/elimination of HNO /cyclization reaction of 2-oxoaldehydes with nitroalkanes bearing various remote functionalities is described. Both chiral and achiral nitroalkanes were applicable to this protocol, leading to a variety of oxacycles, such as chromenes, chromanes, cyclic hemiacetals, and polycyclic acetals. An unexpected regioselective photooxygenation occurred without sensitizer during derivatization to convert a derived diene product into a dioxetane by reaction with singlet oxygen, which provided chromen-2-one and benzaldehyde after fragmentation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01158