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Diastereoselective cycloadditions and transformations of N-alkyl and N-aryl maleimides with chiral 9-anthrylethanol
Harry Adams1, Tareg M Elsunaki, Isaac Ojea-Jiménez
1Department of Chemistry, Dainton Building, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK.
Abstract:
Thermal Diels-Alder reactions of chiral 9-methoxyethyl and 9-hydroxyethyl anthracene have been investigated both experimentally and computationally with a range of N-substituted maleimides. Whereas cycloadditions with 9-methoxyethyl anthracene proceeded with almost complete diastereselectivity, those with 1-anthracene-9-yl-ethanol resulted in essentially no diastereoselectivity. Subsequent regio- and stereoselective transformations with reducing agents and carbon nucleophiles demonstrated the synthetic utility of this methodology, which was applied to the enantioselective synthesis of pyrrolo[2,1-a]isoquinolines and an attempted synthesis of the alkaloid crispine A. Computational studies supported the proposed hypotheses for the stereoselectivity observed in the transformations described.
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