Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral Fused Polycy-clic Compounds

04 December 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in a one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged in a highly regio-, diastereo- and enantiostereoselective Lewis base Asymmetric Allylic Alkylation (AAA) with alkyne functionalized Morita−Baylis− Hillman (MBH) carbonates. Gratefully to the low Lewis base catalyst loading, subsequent gold cata-lyzed Friedel-Crafts type cyclization, entailing the formation of fused polycyclic compounds, proceeded efficiently affording structurally complex highly enantioenriched products.

Keywords

Asymmetric Allylic Alkylation
Lewis Base
Gold Catalysis
Chiral Polycyclic Compounds

Supplementary materials

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Title
Supporting Information: Merging enantioselective Lewis base organocatalysis and gold(I) catalysis: A one-pot access to chiral fused polycyclic compounds.
Description
Experimental procedures, characterization data, copies of NMR spectra and HPLC chromatograms of all new com- pounds and X-ray crystallographic structure of 20 CCDC 2404672. (PDF)
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