Unusual regiochemistry of cycloaddition of ketenes to (R)-2-tert-butyldihydrooxazole derivatives. A simple route towards enantiomerically pure functionalised α-aminocyclobutanones

✍ Scribed by JoséRenato Cagnon; Franck Le Bideau; Jacqueline Marchand-Brynaert; Léon Ghosez

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 232 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00364-x

✦ Synopsis

Ketenes have been found to cycloadd with (R)-2-ten-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-3hydroxycyclobutanones.