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Triethylamine-Promoted Henry Reaction/Elimination of HNO 2 /Cyclization Sequence of Functionalized Nitroalkanes and 2-Oxoaldehydes: Diversity-Oriented Synthesis of Oxacycles.
- Source :
-
Organic letters [Org Lett] 2023 Jun 09; Vol. 25 (22), pp. 4033-4037. Date of Electronic Publication: 2023 May 26. - Publication Year :
- 2023
-
Abstract
- The triethylamine-promoted cascade Henry reaction/elimination of HNO <subscript>2</subscript> /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.
- Subjects :
- Cyclization
Acetals
Benzopyrans
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 25
- Issue :
- 22
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 37235554
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c01158