Events The 13th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 13th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2009

Citation

Teodoro S. Kaufman, Marcela Amongero, ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES, in Proceedings of The 13th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2009, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-13-00211

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ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES

Teodoro S. Kaufman ¹

Marcela Amongero ¹

1. Institute of Chemistry of Rosario and School of Pharmaceutical and Biochemical Sciences, National University of Rosario, Suipacha 531, S2002LRK Rosario, Argentine

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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