ADDITION OF ACRYLAMIDE TO AMINO ALDEHYDES TO GENERATE NON-BAYLIS-HILLMAN ADDUCTS - FORMATION OF NOVEL N-ACYLHEMIAMINALS

Authors
BUSSOLARI JC BEERS K LALAN P MURRAY WV GAUTHIER D MCDONNELL P
Citation
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
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
8
Year of publication
1998
Pages
787 - 788
Database
ISI
SICI code
0366-7022(1998):8<787:AOATAA>2.0.ZU;2-A
Abstract
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.