[3+2] Annulation of N-Ts-α-Amino Aldehydes and 1,3-Bis(silyl)propenes

Significance

The authors describe a stereoselective synthesis of pyrrolidines via a [3+2] annulation with 1,3-bis(silyl)propenes. A number of silyl groups were tested and the Me₂PhSi group was used due to its success as well as its ability to be oxidized under Tamao-Fleming conditions. Of the many Lewis acids tested, aluminium-based acids proved to be the best, with MeAlCl₂ giving optimal results. A number of chiral aldehydes were used and all reactions proceeded with perfect diastereo­selectivity.