In situ generation of N-Boc-protected alkenyl imines: controlling the E/Z geometry of alkenyl moieties in the Mukaiyama-Mannich reaction.

Research paper by Jian-Fei JF Bai, Hajime H Sasagawa, Taiga T Yurino, Taichi T Kano, Keiji K Maruoka

Indexed on: 07 Jul '17Published on: 07 Jul '17Published in: Chemical Communications


Readily available Boc-protected Z-alkenyl aminals could be used as Z-alkenyl and E-alkenyl imine precursors under acidic conditions. In the Mukaiyama-Mannich reaction of Z-alkenyl Boc-aminals, the E/Z geometry of the products was controlled by the catalyst used. The present method was also applied to asymmetric Mukaiyama-Mannich reactions.