An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Peregrina, J.M. 1
  4. Sucunza, D. 1
  5. 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: 9

Pages: 1383-1388

Type: Article

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DOI: 10.1016/S0957-4166(01)00230-0 SCOPUS: 2-s2.0-0035844349 WoS: WOS:000169811600019 GOOGLE SCHOLAR

More publications in: Tetrahedron: Asymmetry

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Abstract

This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultant from protection of the AD products were used as starting materials in the synthesis of O-benzyl ethers of the valuable C4-chiral building blocks (S)- and (R)-2-methylglycidol. © 2001 Elsevier Science Ltd.