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

Hisashi Yamamoto; Isai Ramakrishna

doi:10.1055/a-2518-2534

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml

Share / Bookmark

Facebook Linkedin Weibo

Download PDF

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

Thieme Connect Search in Google Scholar

› Further Information

Abstract
Full Text
Figures

PDF Download Permissions and Reprints

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.

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.

Publication History

Article published online:
25 February 2025

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

Permissions and Reprints