Unusual regiochemistry of cycloaddition of ketenes to (R)-2-tert-butyldihydrooxazole derivatives. A simple route towards enantiomerically pure functionalised alpha-aminocyclobutanones.
Cagnon, José Renato;Le Bideau, Franck;Marchand-Brynaert, Jacqueline;Ghosez, Léon
Ketenes have been found to cycloadd with (R)-2-tert-Butyldihydrooxazole 1 and 2 to yield predominantly regioisomers 4 resulting from steric control rather than electronic control. The cycloadditions provide a practical route to enantiomerically pure protected 2-amino-3-hydroxycyclobutanones. (C) 1997 Elsevier Science Ltd.
Cagnon, J. R., Le Bideau, F., Marchand-Brynaert, J., & Ghosez, L. (1997). Unusual regiochemistry of cycloaddition of ketenes to (R)-2-tert-butyldihydrooxazole derivatives. A simple route towards enantiomerically pure functionalised alpha-aminocyclobutanones. Tetrahedron Letters, 38(13), 2291-2294. https://doi.org/10.1016/S0040-4039(97)00364-X (Original work published 1997)