Synthesis of Vinyl Ketones via Mannich Bases

aldol reaction with formaldehyde is difficult

O
was Nu: O O NMe2
(enolate) aldol
Ph
Ph H H H H
was E+
(C=O) formaldehyde Mannich
Nu:
E+ reagent
-unsaturated
reactive, easier,
ketone TM
unstable better yields
with =CH2 group

synthetic equivalents

the Mannich reaction

O O O
HCl
Me2NH
Ph H H Ph
ketone formaldehyde
NMe2
Mannich base

"aldol"

synthesis of vinyl ketone from Mannich base

O O
CH3I base
Ph Ph
SN2 E2
NMe2
-unsat'd
(vinyl) ketone