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Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts.
Miura, Tomoya; Nakahashi, Junki; Zhou, Wang; Shiratori, Yota; Stewart, Scott G; Murakami, Masahiro.
Afiliación
  • Miura T; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
  • Nakahashi J; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
  • Zhou W; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
  • Shiratori Y; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
  • Stewart SG; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
  • Murakami M; Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
J Am Chem Soc ; 139(31): 10903-10908, 2017 08 09.
Article en En | MEDLINE | ID: mdl-28708391
ABSTRACT
A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2017 Tipo del documento: Article País de afiliación: Japón
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Banco de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2017 Tipo del documento: Article País de afiliación: Japón