[4+2]-Annulations of Aminocyclobutanes

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.


Published in:
Organic Letters, 17, 4, 1030-1033
Year:
2015
Publisher:
Washington, American Chemical Society
ISSN:
1523-7060
Laboratories:




 Record created 2015-04-13, last modified 2018-12-03

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