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Usage Statistics Cite this paper as: Amongero, M.; Kaufman, T. ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES. In Proceedings of the 13th Int. Electron. Conf. Synth. Org. Chem., 1-30 November 2009; Sciforum Electronic Conferences Series, 2009, c011:1-12.
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13th Int. Electron. Conf. Synth. Org. Chem. 2009, c011:1-12
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ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES
Institute of Chemistry of Rosario and School of Pharmaceutical and Biochemical Sciences, National University of Rosario, Suipacha 531, S2002LRK Rosario, Argentine;
* Author to whom correspondence should be addressed.
(This article belongs to the section C. 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
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