a-Methylserinals as an access to a-methyl-ß-hydroxyamino acids: Application in the synthesis of all stereoisomers of a- methylthreonine

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Corzana, F. 1
  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

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Ano de publicación: 2004

Volume: 15

Número: 4

Páxinas: 719-724

Tipo: Artigo

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DOI: 10.1016/J.TETASY.2003.12.001 SCOPUS: 2-s2.0-1042275588 WoS: WOS:000189116300021 GOOGLE SCHOLAR

Outras publicacións en: Tetrahedron: Asymmetry

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Resumo

The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different β-substituted α-methylserines. © 2003 Elsevier Ltd. All rights reserved.