Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation
A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from b-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the b-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.
Additional Information© Royal Society of Chemistry 2009. Received 6th July 2009, Accepted 9th September 2009. First published on the web 6th October 2009. The authors gratefully acknowledge Pamela M. Tadross and Scott C. Virgil for helpful discussions and experimental assistance. The authors thank Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, Sigma-Aldrich and Caltech for generous funding. Electronic supplementary information (ESI) available: General experimental procedures, characterization data, NMR, and IR spectra. See DOI: 10.1039/b913336d
Published - Allan2009p6436Org_Biomol_Chem.pdf
Supplemental Material - b913336d.pdf