Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates.

Keliher, Edmund J; Burrell, Richard C; Chobanian, Harry R; Conkrite, Karina L; Shukla, Rajesh; Baldwin, John E

Keliher, Edmund J; Burrell, Richard C; Chobanian, Harry R; Conkrite, Karina L; Shukla, Rajesh; Baldwin, John E.

Afiliación

Keliher EJ; Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Box 234, Cambridge, MA 02138, USA.

Org Biomol Chem ; 4(14): 2777-84, 2006 Jul 21.

Article en En | MEDLINE | ID: mdl-16826303

RESUMEN

Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with alpha-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2-phenylcyclopropanecarboxylates (the 1-d-3-(13)C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized.

Asunto(s)

Ácidos Carboxílicos/química; Ciclopropanos/química; Ciclopropanos/síntesis química; Isótopos de Carbono; Catálisis; Cobre/química; Estructura Molecular; Estereoisomerismo; Estireno/química

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Carboxílicos / Ciclopropanos Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2006 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido

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