[4 + 2]-Annulations of aminocyclobutanes.
- Perrotta D Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
- Racine S
- Vuilleumier J
- de Nanteuil F
- Waser J
- 2015-02-05
Published in:
- Organic letters. - 2015
English
The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using scandium triflate or iron trichloride as catalyst. The use of thymine- or fluorouracil-substituted cyclobutanes gave direct access to six-membered ring nucleoside analogues. Finally, the [4 + 2]-annulation between aminocyclobutanes and enol ethers led to the corresponding cyclohexylamines.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1021/acs.orglett.5b00149
- PMID 25650887
- Persistent URL
- https://sonar.ch/global/documents/194197
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