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Expanding the Chiral Monoterpene Pool: Enantioselective Diels-Alder Reactions of α-Acyloxy Enones.
Mendoza, Skyler D; Rombola, Michael; Tao, Yujia; Zuend, Stephan J; Götz, Roland; McLaughlin, Martin J; Reisman, Sarah E.
Afiliación
  • Mendoza SD; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Rombola M; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Tao Y; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Zuend SJ; BASF Corporation, 46820 Fremont Boulevard, Fremont, California 94538, United States.
  • Götz R; BASF SE, Carl Bosch Str. 38, Ludwigshafen 67056, Germany.
  • McLaughlin MJ; BASF SE, Carl Bosch Str. 38, Ludwigshafen 67056, Germany.
  • Reisman SE; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Org Lett ; 24(21): 3802-3806, 2022 06 03.
Article en En | MEDLINE | ID: mdl-35594569
An enantioselective Diels-Alder (DA) reaction of α-acyloxy enones has been developed to synthesize chiral oxidized cyclohexenes. Yttrium(III) triflate, in conjunction with a chiral pyridinebisimidazoline (PyBim) ligand, was found to catalyze the asymmetric [4 + 2] cycloaddition with a variety of dienes and α-acyloxy enone dienophiles. Using this method, terpinene-4-ol, a key intermediate in the synthesis of commercial herbicide cinmethylin, can be prepared in four steps from isoprene. A combination of kinetic data and NMR studies support a mechanism involving reversible binding of a dienophile to a yttrium catalyst followed by cycloaddition with a diene as the rate-determining step.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Polienos / Monoterpenos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Polienos / Monoterpenos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos