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Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation.
Gladfelder, Joshua J; Ghosh, Santanu; Podunavac, Masa; Cook, Andrew W; Ma, Yun; Woltornist, Ryan A; Keresztes, Ivan; Hayton, Trevor W; Collum, David B; Zakarian, Armen.
Afiliação
  • Gladfelder JJ; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Ghosh S; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Podunavac M; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Cook AW; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Ma Y; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Woltornist RA; Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
  • Keresztes I; Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
  • Hayton TW; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
  • Collum DB; Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
  • Zakarian A; Department of Chemistry and Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
J Am Chem Soc ; 141(38): 15024-15028, 2019 09 25.
Article em En | MEDLINE | ID: mdl-31460756
ABSTRACT
Direct enantioselective α-alkylation of 2-alkylpyridines provides access to chiral pyridines via an operationally simple protocol that obviates the need for prefunctionalization or preactivation of the substrate. The alkylation is accomplished using chiral lithium amides as noncovalent stereodirecting auxiliaries. Crystallographic and solution NMR studies provide insight into the structure of well-defined chiral aggregates in which a lithium amide reagent directs asymmetric alkylation.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos Organometálicos / Piridinas / Lítio Idioma: En Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Compostos Organometálicos / Piridinas / Lítio Idioma: En Ano de publicação: 2019 Tipo de documento: Article