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Synfacts 2019; 15(01): 0095
DOI: 10.1055/s-0037-1611428
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of α-Aryl Amino Acids

Contributor(s):
Hisashi Yamamoto
,
Wataru Muramatsu
Leonard D, Ward JW, Clayden J. * University of Bristol, UK
Asymmetric α-Arylation of Amino Acids.

Nature 2018;
562: 105-109
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Further Information

Publication History

Publication Date:
14 December 2018 (online)

 
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Key words

arylation - quaternary amino acids - potassium bistrimethylsilylamide - stereoselectivity - aryl amino acids

Significance

Quaternary amino acids play an important role as modifiers of peptide conformation and bioactivity. The authors describe an α-arylation of enantiopure amino acid precursors to form quaternary centers.


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Comment

This KHMDS-mediated α-arylation of enantiopure amino acid precursors proceeds smoothly to provide quaternary amino acids in high yields and without significant loss of stereochemical integrity.


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