Events The 2nd International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 2nd International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 1998

Citation

Marco A. Montaos, Eduardo Fernàndez-Megîa, Celia Penide, Enantiospecific, Stereoselective Synthesis of Enantiomerically Pure Aziridine-2-carboxylic Acids from Aspartic Acid, in Proceedings of The 2nd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1998, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-2-01673

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Enantiospecific, Stereoselective Synthesis of Enantiomerically Pure Aziridine-2-carboxylic Acids from Aspartic Acid

Marco A. Montaos ¹

Eduardo Fernàndez-Megîa ¹

Celia Penide ¹

1. Departamento de Química Orgánica. Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain

Abstract

Enantiomerically pure aziridine-2-carboxylates containing a CH2OMs group, and azetidine-3-mesyloxy-2- carboxylates were prepared by cyclization of 2-amino-3,4-dimesyloxybutyrates, stereoselectiveprepared from aspartic acid. The outcome of the cyclization was dictated by the configuration of the C-3 stereogenic center. The mesylate group of the aziridino mesylates could be displaced by nucleophiles without opening of the aziridine ring.

Keywords

Aziridine-2-carboxylic acids

azetidine-2carboxylic acids

aziridine ring formation

azetidine ring formation.

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