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Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives

✍ Scribed by Alberto Avenoza; Jesús H. Busto; Carlos Cativiela; Jesús M. Peregrina; David Sucunza; Marı́a M. Zurbano

Book ID
104359610
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
290 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

This report describes the synthesis of the two enantiomerically pure a-methylated b-branched phenylalanine derivatives, (S)-and (R)-a-methyl-b,b-diphenylalanine-(aMe)Dip-starting from the chiral building blocks (R)-and (S)-N-Boc-N,O-isopropylidene-a-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other a-methylated b-branched serine derivatives is also described.

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