Synthesis of enantiopure (aMe)Dip and other a-methylated ß-branched amino acid derivatives

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  4. Peregrina, J.M. 1
  5. Sucunza, D. 1
  6. Zurbano, M.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Aldizkaria:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Argitalpen urtea: 2003

Alea: 14

Zenbakia: 3

Orrialdeak: 399-405

Mota: Artikulua

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DOI: 10.1016/S0957-4166(02)00828-5 SCOPUS: 2-s2.0-0037423123 WoS: WOS:000180820400016 GOOGLE SCHOLAR

Beste argitalpen batzuk: Tetrahedron: Asymmetry

Gordailu instituzionala: lock_openSarbide irekia Editor

Laburpena

This report describes the synthesis of the two enantiomerically pure α-methylated β-branched phenylalanine derivatives, (S)- and (R)-α-methyl-β,β-diphenylalanine - (αMe)Dip - starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-α-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 α-methylated β-branched serine derivatives is also described. © 2003 Elsevier Science Ltd. All rights reserved.