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

Marco Montaos; Eduardo Fernàndez-Megîa; Celia Penide

doi:10.3390/ecsoc-2-01673

Previous Article in event

3-(2-Alkylsulfanyl-6-benzothiazolylaminomethyl)-2-benzoxazolethiones. Synthesis and Photosynthesis-inhibiting Activity in Spinach Chloropasts

Next Article in event

Use of a new hydrophilic phosphonic phosphines (DPPA). Heck Reaction in Aqueous Medium under Microwave Irradiation.

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

Marco A. Montaos

Eduardo Fernàndez-Megîa

Celia Penide

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

Published: 01 November 1998 by MDPI in The 2nd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-2-01673

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.

View paper

63 Reads
0 Recommendations

Marco Montaos

Eduardo Fernàndez-Megîa

Celia Penide