Asymmetric Hydroxylation of (S,S)-(+)-Pseudoephedrine Phenylacetamide Enolates

  1. Reyes, Efraim 1
  2. Carrillo, Luisa 1
  3. Vicario, Jose 1
  4. Badía, Dolores 1
  1. 1 Universidad del País Vasco/Euskal Herriko Unibertsitatea
    info

    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

Revista:
Letters in Organic Chemistry

ISSN: 1570-1786

Año de publicación: 2004

Volumen: 1

Número: 4

Páginas: 331-334

Tipo: Artículo

DOI: 10.2174/1570178043400569 WoS: WOS:000226130300008 GOOGLE SCHOLAR lock_openAcceso abierto editor

Otras publicaciones en: Letters in Organic Chemistry

Resumen

Enantioenriched α-hydroxy acids and esters have been synthesized by oxidation of (S,S)-(+)- pseudoephedrine arylacetamide enolates with different reagents. We have found that the oxidation of these enolates proceeds with good yields and diastereoselectivities and, interestingly, we have also noticed that the use of different oxidation reagents allows the selective preparation of any of the two possible epimers of the target α-hydroxy amides. We have also optimized a mild procedure for the removal of the chiral auxiliary and therefore for the obtention of enantioenriched α-hydroxy acids, which were also easily converted into the corresponding α-hydroxy esters. The developed methodology becomes a promising field of research due to the potentiality of the reaction, which a priori should allow the stereodivergent synthesis of a wide variety of α-hydroxy carbonyl compounds.