Electrophile dependent mechanisms in the asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl)azetidine

Abstract

Sn–Li exchange and ‘poor man's Hoffmann tests’ establish asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl) (Botc) azetidine to be controlled by dynamic thermodynamic resolution or dynamic kinetic resolution, depending on the electrophile. Unusually, different configurational stability is seen for the anion generated by lithiation compared to transmetallation. Configurational stability of α-lithio-N-Boc azetidine indicates instability with the N-Botc system is due to the CS group.