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Synfacts 2025; 21(03): 328
DOI: 10.1055/a-2518-2534
Peptide Chemistry

PTC-Catalyzed Asymmetric Alkylation of Glycine Imines for the Synthesis of Unnatural Amino Acid Esters

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna 
Lygo B, Allbutt B *. University of Nottingham, UK
Asymmetric PTC Alkylation of Glycine Imines: Variation of the Imine Ester Moiety.

Synlett 2004; 326-328
DOI: 10.1055/s-2003-43368
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Keywords

asymmetric alkylation - glycine imines - alkyl bromides - unnatural amino esters

Significance

Asymmetric alkylation is a powerful tool in organic synthesis to synthesize optically active molecules. In 2004, Lygo et.al developed a quaternary-ammonium-derived phase-transfer-catalyst-catalyzed asymmetric alkylation of glycine imines for the synthesis of unnatural amino acid esters.


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Comment

A series of unnatural amino acid esters were synthesized by asymmetric phase-transfer alkylation of various glycine imine esters. This reaction proceeded smoothly to deliver the desired products in good yields and with excellent optical purities.


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Publication History

Article published online:
25 February 2025

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