Science of Synthesis

Bernardi, L.; Ricci, A., Science of Synthesis: Multicomponent Reactions, (2014) 1, 123.

General Introduction

The one-pot formation of optically active β-amino carbonyl compounds (Mannich bases) from the reaction of an enolizable ketone with formaldehyde and an amine was first recognized by Mannich.[‌1‌] In practice, enolizable aldehydes or ketones serve as the CH-acidic substrate for direct Mannich reactions (‌Scheme 1‌). The Mannich reaction is one of the most useful reactions for the synthesis of nitrogen-containing compounds as well as an effective method for the construction of C—C bonds.[‌2‌]

‌Meeeee 8‌ Mee Meeee-Meeeeeeee Meeeee Meeeeee Meeeeeee

Mee eeeeeeeeeee eeeeeeeeeeeeee ee eee eeeee eeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeee eeee ee eeeeeee eeeee ee eeeeeeeeeee, eeeeeeeee eeeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeee. Meeeeee eeee eee eeee ee eee eeeee eeeeeeeeee (eeeeeeee eeeee, eeeee, eee eeeeeeee eeeeeeee) ee eee eeeeee Meeeeee eeeeeeee eeeeeeeeeee e eeeee eeeeeeeee. Me eeeeeeee, eeee eeeeeeeee eeee ee eee eeeeeeeeeeeee eeeee eeeeeeee eeeee eeeee, eeee eeeeeeee eee eeeeee. Meeeee eeeee eee Meeeeee eeeeeeeee eeeeeeeee eeeeeee, eee eeeee eeeee eeeeee ee eee eeeeeeeeeee eeeee eeeeeee eee eeeeeeee eee eee eeeee, eee ee eeeee eeeeeeeeee eeee eeeeeeeee (‌Meeeee 8‌). Mee eeeeeeeeeeeee ee eee Meeeeee eeeeeeee eee eee eeeeeeeeeee ee eee eeeee eeeeeeeee eeee eee β-eeeee eeeeeeee eeeeeeee eeeeeee e eeeee-eee-Meeeeee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeeee.

‌Meeeee 8‌ Meeeee Meeeeee Meeeeeee eee Meeeeeeee Meeee Meeeeeee

Meee ee eeeee eeeeee eeee eeee eeeeeeeee eeeeeeeee eeeeeee eee eeeeeeeeee ee e eee-eeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeee, ee ee eee eeeeeeeeeee ee eeeeeeee Meeeeee eeeeeeee eeee eeeeeeeee eeeeeeee (eeeeee eeeee eeeeeeee) eeee eeeeee eee eeeeeeee eeee ee eeee eeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeee (‌Meeeee 8‌). Meeeeeeeeee, ee eeeeeeeeee eee eeeeeee eeeeeeeeee ee eeeee eeeeeeeeee, eeeeeeeeee Meeeeee eeeeeeeee eeee eeee eeeeeeeee eeeee ee eeeee eeeeeeee π-eeeeeeeeeeee (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeee Meeee-Meeeeeeee Meeeeee Meeeeeee eee Mee Meeeeeeeee Meeeeeeeeee

Meee ee eee eeeee-eeeeeeeee Meeeeee eeeeeeeee eeee eeeee eeeee eeeeeeeee eeeeeeeee ee Meeee eee Meøeeeee eeeee, eeeeeeee eeeee eeee ee eeeeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeeeeeee/eeeeeeeeeee, ee eeee ee eeeeeeeee eeeee eeeeeeeee. α-Meeee eeeee, eeeee eee eeee ee eeeeeeee eee eeeeeeee eeeee eeeeeee eee eeeeeeeee ee ee eeeeeee eeeeeeeeeeee, eee eeee eeee eeeeeeeeee eeeeeeeee eee eeeeee Meeeeee eeeeeeeee. Me ee eeeee eeeeeeeeee eeee eeeeeee eee eeeeeeee eeeeeeeeeeee ee eeeeeee eeeeee eeeeee, eee eeeeeeeee eeeeeeee eeee ee ee eeeeeeee ee eee eeeee eeeeeeeee eeeeee eeeee eeeeeeeee ee eeeee ee eeee eeeeee, eeee eeeeee e eeeeeee eeeeeeeee ee eee eeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeeeeeee.

Mee Meeeeee eeeeeeee ee eeeeee eeee eeeeeeeeee eee eeeeeeeee eee eeeeeee ee eeeeeeeeeeeee eeee. M eeee eeeeeee ee eeeeeee eeeeeeee eee eeeee eeeeeeeeee eeeeeeeee eeeeee, eeeeeeee-eeeeeeeeee eeeeeeeee (eeeeeeee, eeeeeee eeeee, eeeeeeeeeeee eeeeee eeeeeeeee) eeee eeeeeeeee eeeeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeee eeeeeeee,[‌8‌] eeeee eee eeee eeeeeeeeee eee eeeeeeeeeee ee eeeeeeeee eeeeeeeeee Meeeeee eeeeeeeee ee eeee eeeeee eeeee.[‌8‌] Mee eeeeeeeeeee ee eeeeee Meeee eeee eeeeeeeee eeeee eeee ee 8888[‌8‌] eee eee eeeeeeee eee ee 8888[‌8‌] eee eee eeeeee eeeeeee ee eee eeeeeeeeeeeeeeee Meeeeee eeeeeeee eeee eeeeeeeee eeeeee. Meeeeee, ee eee eee eeeee eee eeeeeeeeee ee eeeeeeeeeeeeeee, eeeeeeeeeeeee ee eee eeee-eeeee eeeee eeeeeeeee, eeee eee eeeeeeeee eeeeeeeeee eeeeeeeeeeeeee Meeeeee eeeeeeee eeeee ee eeeeeeee. Meeeee ee eee eeeeeeeeee eeee ee eeeeeee-eeeeeeeee Meeeeee eeeeeeeee,[‌8‌,‌8‌] α-eeeee eeeee eee eee ee eeeeeeeeee eeee eeeeeeeee eeeeeeeee eee eeee eeeeeeeeeeeeee, eeeeeee ee eee eeee eeeeeeee eeeeeeeee 8,8′-ee-8-eeeeeeee-eeeeeee eeeeeeeeee eeeee.[‌8‌]

Meeeeeeee eeeeeee ee eeee eeeeeee Meeeeee eeeeeeeee eeeeeee eee eeeeeeeee eeeeee eee eeeeeeeee eeeeeeeee. Meeeeee, eeeeeee e eeee eeeee ee eeeeee eee eeeeeee eeeeee, eeeeeeee, eee eeeee eeeeee eeeeeeee eeee eeeeeeee eeeeeeeee eee ee eeeeeee ee eeeee eeeeeeeee, eee eeeee ee eeeee eeeeeeeeee ee eeeee eeeeee. Meeeeeeeeeee ee eeeeeeee eee eeeeee eeeeee eee eeeee eeeeeeeeeeee eeeee eee eeeeeeee eee eeeee eeeee, eeee eee 8-eeeeeeeeeeeee eeeee eeeee eee eeee eeeeee eeee. Meee, eee eeeee eeeeeeeeeee ee eeeee eee eeeeeeeeee ee e eeeeeeee eee eeeeeeee eeeeeeeee eeeeee e eeeeeeeeeeeeee eeeeeee, eee eeeeee ee e eeeeeeeeee eeeee ee eee eeeeeeee eeee ee eee eeeeeee. Meeeeeeeeee, eeee eeeeee eeeee eeeeeee eeeeeeeee eee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeee Meeeeee eeeeeeeee eeee eeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeee. Meee eeeeeeee eeeeee eee eeeeeeee eeeeeeeeee, eee eeeeeee eee eeeeeeeeee eeeeeeeee eeeeeeeeee eeee eeeee eeeeeeeeee eeeeeeeee. Meeeeee, ee ee eeeee eeeeeeeee eeee eee ee eee eeeeeeee eeeeeeeeeee ee eeeee eeeeeeeeee eee/ee eeeeeeeeeeeeee eeeeeeeee eeeeee eee eeeee ee eeeeeeeee Meeeeee eeeeeee ee ee eeeeeeee ee eeee eeeeeeeeeeee eeeeeeeee eeeeeeeee, eeeeeeee eee eeeeeee eeeeeeeee eeeeeeeeeeeee.

References