Synthesis of 2-amino-1,3-diols incorporating the cyclobutane ring

  1. Pérez-Fernández, M. 1
  2. Avenoza, A. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  5. Rodríguez, F. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Any de publicació: 2008

Volum: 64

Número: 38

Pàgines: 9088-9092

Tipus: Article

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DOI: 10.1016/J.TET.2008.07.016 SCOPUS: 2-s2.0-48549094668 WoS: WOS:000259045100008 GOOGLE SCHOLAR

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Resum

The synthesis of free and protected 2-amino-1,3-diols with threoninol substructure that incorporate a conformational restriction defined by the cyclobutane ring is reported. The key step in the synthesis of these target compounds, namely cis- and trans-c 4-threoninols, is the addition of methylmagnesium bromide to a cyclobutanone derivative. The selectivity of the reaction is modulated by the solvent. © 2008 Elsevier Ltd. All rights reserved.