Jc. Bussolari et al., ADDITION OF ACRYLAMIDE TO AMINO ALDEHYDES TO GENERATE NON-BAYLIS-HILLMAN ADDUCTS - FORMATION OF NOVEL N-ACYLHEMIAMINALS, Chemistry Letters, (8), 1998, pp. 787-788
Aldol reactions of chiral aminoaldehydes and methylacrylate in the pre
sence of 1,4-diazabicyclo[2.2.2]octane (DABCO) produces beta-hydroxp m
ethylbutenoates which can be utilized as psuedodipepetides. However, r
eaction of aminoaldehydes with acrylamide in the presence of DABCO aff
orded the adducts derived from the addition of the acrylamide nitrogen
to the aldehyde to generate N-acylhemiaminals. These reactions were f
ound to proceed at a faster rate than the typical Baylis-Hillman react
ion and also require the presence of DABCO.