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Synfacts 2025; 21(10): 1070
DOI: 10.1055/a-2680-8013
Peptide Chemistry

1,4-Conjugate Addition of Alkyl Iodides with Chiral Methyleneoxazolidinone to Access α-Amino Acids

Authors

Suárez RM, Sestelo JP *, Sarandeses LA *. Universidade da Coruña, Spain
Practical and Efficient Enantioselective Synthesis of α-Amino Acids in Aqueous Media.

Org. Biomol. Chem. 2004;
2: 3584-3587
DOI: 10.1039/B413017K
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Keywords

methyleneoxazolidinone - 1,4-conjugate addition - zinc - copper iodide - amino acids

Significance

The development of new methods for the synthesis of natural and unnatural amino acids has gained great attention in the peptide drug development industry because they are key motifs in target peptide synthesis. In 2004, the authors developed a method for synthesizing enantiomerically pure natural and unnatural amino acids from chiral methyleneoxazolidinone.


 

Comment

The zinc/copper-mediated 1,4-conjugate additions of alkyl iodides with chiral methyleneoxazolidinone proceeded in a highly diastereoselective fashion to offer the corresponding amino acids with high optical purity. This reaction proceeded rapidly under mild conditions with excellent yields.


 

 

Publication History

Article published online:
23 September 2025

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