Amino-indanol catalyzed enantioselective reactions of 3-hydroxy-2-pyridones.
A new bifunctional catalyst, chiral amino-indanol 1a, containing both Brønsted base and hydrogen bonding donor moieties, has been identified. It is easily prepared in a single step from commercially available amino-indanol. It was found to be an excellent catalyst for Diels-Alder reactions of both 3-hydroxy-2-pyridone and 3-hydroxy-2-pyrone. Various dienophiles including N-substituted maleimides were investigated. The Diels-Alder adducts were obtained in excellent yields and high enantioselectivities.
Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543.
Julian Ying-Teck
JY
Soh
Choon-Hong
CH
Tan