ChemInform Abstract: A Novel Synthesis of Enantiopure Octahydropyrrolo[3,4-b]pyrroles by Intramolecular [3 + 2] Dipolar Cycloaddition on Chiral Perhydro-1,3-benzoxazines.

  1. Pedrosa, Rafael 1
  2. Andres, Celia 1
  3. de las Heras, Laura 1
  4. Nieto, Javier 1
  1. 1 Universidad de Valladolid
    info

    Universidad de Valladolid

    Valladolid, España

    ROR https://ror.org/01fvbaw18

Revista:
ChemInform

ISSN: 0931-7597,  1522-2667

Año de publicación: 2010

Volumen: 33

Número: 47

Páginas: no-no

Tipo: Artículo

DOI: 10.1002/CHIN.200247149 GOOGLE SCHOLAR lock_openAcceso abierto editor

Otras publicaciones en: ChemInform

Resumen

1,3-Oxazine derivatives (II), obtained as singlediastereomers from (-)-8-aminomenthol via condensation with glycolaldehydedimer, alkylation of the resulting 2-hydroxymethyl perhydrobenzoxazineproduct with alkenyl bromides, and Swern oxidation of the alcohols, affordwith glycine derivatives (III) and (VIII) the cycloadducts (IV) and (IX) withcomplete regio- and diastereoselectivity. It is assumed that the cycloadductsare formed via condensation of oxazines (II) with the glycines, followed bydecarboxylation to provide azomethine ylides, and final intramolecular [3 + 2]cycloaddition. The yields are dependent on the reaction temperature and thepresence or absence of a base. The menthol moiety of compound (IV) is cleavedto afford fused pyrrole (VII).

Referencias bibliográficas

  • Pedrosa, (2002), Org. Lett., 4, pp. 2513, 10.1021/ol0261377