Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions.
A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan-2-ones with alkyl vinyl ketones in the presence of a catalytic amount of l-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the asymmetric synthesis of privileged bicyclic lactones through kinetic resolution and show the synthetic application to pharmaceuticals and natural products synthesis.
Ramachary
Dhevalapally B
DB
School of Chemistry, University of Hyderabad, Hyderabad-500 046, India. ramsc@uohyd.ernet.in
Kishor
Mamillapalli
M
D000478:Alkylation; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D011392:Proline / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism
C517737:9-amino-9-deoxyepiquinine; D001572:Benzofurans; D011807:Quinolizines; D011392:Proline