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Synthesis and Ring Opening of Methyl 2-Alkyl-3-(alkyl/aryl)-1-benzoylaziridine-2-carboxylates: Synthesis of Polysubstituted Amino Acids (2000)

Papa, Carmela ; Tomasini, Claudia

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1569-1576

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ISSN: 1434-193X

Keywords: Aziridines ; Oxazolines ; Ring expansion reactions ; Amino acids ; Amino acids ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---A new method for the preparation of 2,2,3-trisubstituted methyl 1-benzoylaziridine-2-carboxylates is reported. These compounds have been obtained starting from α-alkyl β-amino acids by formation of the lithium dianion and reaction with iodine. The aziridines undergo ring expansion or ring opening, depending on the substituents of the aziridine ring and on the reaction conditions. Following these methods, both α-substituted α-hydroxy β-amino acids and α-substituted β-hydroxy α-amino acids have been synthesised.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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