One-pot three-component reaction of fluoroalkanesulfonyl azide, vinyl ether and aldehyde: the formation of polysubstituted fluorinated oxazolidines

Efficient and diastereoselective synthesis of highly substituted fluorinated oxazolidines was achieved via a one-pot three-component reaction of fluoroalkanesulfonyl azides , vinyl ether and various aldehydes at 0 °C within 10 min in moderate to good diastereoselectivities (syn/anti). A competing process could be involved in the initial step and an unstable fluorinated aziridine was postulated as the intermediate for these reactions. Additionally, rational transition states were also proposed to elucidate the diastereoselectivities. This synthetic method provides a convenient and expeditious access to N-per(poly)fluoroalkanesulfonyl oxazolidines.