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.
Supplementary materials
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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Supplementary weblinks
Title
NMR data of pure compounds
Description
These data are the primary NMR FID files of all new compounds of this study
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