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Model for the Enantioselectivity of Asymmetric Intramolecular Alkylations by Bis-Quaternized Cinchona Alkaloid-Derived Catalysts.
He, Cyndi Qixin; Simon, Adam; Lam, Yu-Hong; Brunskill, Andrew P J; Yasuda, Nobuyoshi; Tan, Jiajing; Hyde, Alan M; Sherer, Edward C; Houk, K N.
Afiliação
  • He CQ; Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
  • Simon A; Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
  • Lam YH; Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
  • Brunskill APJ; Department of Process Chemistry, Merck and Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
  • Yasuda N; Department of Process Chemistry, Merck and Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
  • Tan J; Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology , Beijing 100029, China.
  • Hyde AM; Department of Process Chemistry, Merck and Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
  • Sherer EC; Department of Process Chemistry, Merck and Co., Inc. , P.O. Box 2000, Rahway, New Jersey 07065, United States.
  • Houk KN; Department of Chemistry and Biochemistry, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
J Org Chem ; 82(16): 8645-8650, 2017 08 18.
Article em En | MEDLINE | ID: mdl-28731701
ABSTRACT
A model for the stereoselectivity of intramolecular alkylations by N,N'-disubstituted cinchona alkaloids reported by Xiang et al. was established using density functional theory (DFT) calculations. The stereocontrol is based on the minimal distortion of the transition state (TS) and catalyst required to achieve favorable electrostatic interactions in the favored TS. Counterions must be included in computational modeling of ion-paired catalysis in order to reproduce experimental enantioselectivity.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos de Espiro / Alcaloides de Cinchona Idioma: En Ano de publicação: 2017 Tipo de documento: Article
Texto completo
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XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos de Espiro / Alcaloides de Cinchona Idioma: En Ano de publicação: 2017 Tipo de documento: Article