Chemoenzymatic synthesis of chiral 2,2 '-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes

Derek Boyd, Narain Sharma, Lenuta Sbircea, D. Murphy, John Malone, S.L. James, Christopher Allen, John Hamilton

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A series of enantiopure 2,2'-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2'-bipyridines were found to be useful chiral ligands for the asymmetric aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-> 84%ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-> 86%ee).
Original languageEnglish
Pages (from-to)1081-1090
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number5
DOIs
Publication statusPublished - 2010

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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