Enantioselective synthesis of (S)- and (R)-alfa-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-alfa-methylserinals

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  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

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Journal:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Year of publication: 2001

Volume: 12

Issue: 6

Pages: 949-957

Type: Article

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DOI: 10.1016/S0957-4166(01)00159-8 SCOPUS: 2-s2.0-0035902418 WoS: WOS:000169012900020 GOOGLE SCHOLAR

More publications in: Tetrahedron: Asymmetry

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Abstract

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks. © 2001 Elsevier Science Ltd.