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

doi:10.1002/(SICI)1099-0690(200004)2000:8<1569::AID-EJOC1569>3.0.CO;2-X

Paper

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

Published Apr 1, 2000 · Carmela Papa, C. Tomasini

European Journal of Organic Chemistry

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Abstract

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.

Study Snapshot

This study presents a new method for preparing 2,2,3-trisubstituted methyl 1-benzoylaziridine-2-carboxylates, enabling the synthesis of polysubstituted amino acids with different substituents and reaction conditions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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"Orthogonal" Lewis acids can catalyze ring-opening and rearrangement reactions of acylaziridines, providing useful synthetic intermediates.

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Citations

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Engineered L-serine hydroxymethyltransferase from Streptococcus thermophilus for the synthesis of α,α-dialkyl-α-amino acids.

The engineered L-serine hydroxymethyltransferase from Streptococcus thermophilus effectively synthesizes diverse,-dialkyl--amino acids, offering potential for biomedical applications.

Regio‐controlled and Stereo‐controlled Ring Expansion of N‐Substituted‐2 Benzoylaziridines Using Fe(NO3)3

This study demonstrates a regio-controlled and stereo-controlled synthesis of trans-4-benzoyl-2,5-diaryl oxazolines using iron (III) nitrate at room temperature, with a plausible mechanism for ring expansion.

Fe(NO3)3 as an efficient catalyst for regio- and stereo-controlled ring expansion of 1,2-diaroyl-3-arylaziridines

This study demonstrates the efficient synthesis of trans-4-benzoyl-2,5-diaryl oxazolines using iron (III) nitrate at room temperature, with a proposed mechanism for ring expansion of N-acyl aziridines to oxazolines.

Regio- and stereo-controlled isomerization of 1,2-diaroyl-3-aryl aziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide

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