Organocatalytic Asymmetric Hetero-Diels–Alder Reaction of in Situ Generated Dienes: Access to α,β-Unsaturated δ‑Lactones Featuring CF3‑Substituted Quaternary Stereocenter
journal contributionposted on 2020-01-28, 18:06 authored by Harshit Joshi, Ankit Yadav, Arko Das, Vinod K. Singh
Chiral bifunctional urea-catalyzed asymmetric direct hetero-Diels–Alder reaction between alkylidene azlactone-derived dienes and trifluoromethyl aryl ketones is reported for the first time. The direct hetero-Diels–Alder reaction followed by ring opening results in densely functionalized α,β-unsaturated δ-lactones featuring a CF3-substituted quaternary stereocenter in high yields with excellent enantioselectivities. The method is compatible over a range of substrates. Moreover, the reaction is scaled up and the α,β-unsaturated δ-lactones were converted to amino acid derivatives decorated with trifluoromethylated carbinol functionality.