2011, Publicación

Mantecón et al. Arkivoc. 2010;2011(3):. Ethyl 4,4-dimethyl pyroglutamate (DMPG): A chiral auxiliary in cyclopropanation and carbonyl group activator.

Publicaciones > Mantecón et al

Arkivoc. 2011;(3), 42-53. doi: 10.3998/ark.5550190.0012.305

Ethyl 4,4-dimethyl pyroglutamate (DMPG): A chiral auxiliary in cyclopropanation and carbonyl group activator.

S. Mantecón1, 2, J.J. Vaquero, P.G. Losada, M.L. De La Puente, J.F. Espinosa, A. Rivera-Sagredo, J. Ezquerra

1. Departamento de Química Orgánica, Universidad de Alcalá, Campus Universitario, 28871-Alcalá de Henares, Madrid, Spain.  2. Centro de Investigación Lilly, Avda. de la Industria, 30, 28108-Alcobendas, Madrid, Spain.

Resumen

Reaction of ethyl (S)-N-trans-2-butenoyl-4,4-dimethyl pyroglutamate with ethyl (dimethylsulfuranylidene) acetate (EDSA) or with Trost's ylide gave rise to stereoselective cyclopropanation, promoted by the chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG), which can easily be removed from the highly functionalised cyclopropanated products using various nucleophiles. © ARKAT USA, Inc.