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ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES
Published: 01 November 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products
Abstract: A concise approach towards trisubstituted optically active azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the L-proline organocatalyzed three component reaction between substituted benzaldehydes, anilines and an enolizable aldehyde, followed by the in situ reduction of the resulting β-aminoaldehydes to the corresponding β-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates.
Keywords: chiral azetidines, enantioselective synthesis, organocatalysis, ring-closing reactions