Addition of Acrylamide to Amino Aldehydes to Generate Non-Baylis-Hillman Adducts. Formation of Novel N-Acylhemiaminals

Abstract

Abstract Aldol reactions of chiral aminoaldehydes and methylacrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) produces β-hydroxy methylbutenoates which can be utilized as psuedodipeptides. However, reaction of aminoaldehydes with acrylamide in the presence of DABCO afforded the adducts derived from the addition of the acrylamide nitrogen to the aldehyde to generate N-acylhemiaminals. These reactions were found to proceed at a faster rate than the typical Baylis-Hillman reaction and also require the presence of DABCO.