Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Dihydroquinolinones.

Author(s) Trost, B.M.; Nagaraju, A.; Wang, F.; Zuo, Z.; Xu, J.; Hull, K.L.
Journal Org Lett
Date Published 2019 Mar 15
Abstract

A palladium-catalyzed decarboxylative asymmetric allylic alkylation (Pd-DAAA) of benzo-fused and non-benzo-fused δ-valerolactams is disclosed. This methodology gives access to chiral lactams bearing C3-quaternary stereocenters, which are central to many natural products and biologically active compounds. The reaction proceeds via palladium-catalyzed ionization of an allyl ester, followed by carbon dioxide extrusion and recombination of the electrophilic Pd-π-allyl complex with the in situ generated lactam enolate. This final step converts racemic allylic ester starting materials into enantiomerically enriched substituted lactams with high yield and enantiomeric excess.

DOI 10.1021/acs.orglett.9b00358
ISSN 1523-7052
Citation Trost BM, Nagaraju A, Wang F, Zuo Z, Xu J, Hull KL. Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Dihydroquinolinones. Org Lett. 2019;21(6):1784-1788.