The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.
- Diels-Alder reaction
- Enantioselective organocatalysis
- Primary β-amino alcohol