Addition of acrylamide to amino aldehydes to generate non-Baylis-Hillman adducts. Formation of novel N-acylhemiaminals

摘要

Aldol reactions of chiral aminoaldehydes and methylacrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) produces beta-hydroxp methylbutenoates which can be utilized as psuedodipepetides. 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. [References: 23]