A practical asymmetric conjugate addition to cyclic enones with chiral bifunctional Ru amido catalysts

Pavel A. Dub, Hui Wang, Masahito Watanabe, Ilya D. Gridnev, Takao Ikariya

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A practical asymmetric C-C bond formation to synthetically useful β-chiral cyclic ketones (>99% ee) using bifunctional chiral amido Ru catalysts under an S/C = 1000, the highest ratio achieved so far in the literature for this class of reactions, is described. The catalytic reactivity decreases in the order of Ru(Msdpen)(hmb) > Ru(Pfbsdpen)(hmb) > Ru(Tsdpen)(hmb) > Ru(PMsdpen)(hmb), where Ru(Pfbsdpen)(hmb) is a newly developed chiral bifunctional catalyst. Complex Ru(Msdpen)(hmb) was identified as the best in terms of reactivity and enantioface selectivity, whereas Ru(PMsdpen)(hmb) gave unsatisfactory results. An importance of the NH proton in the bifunctional catalyst for determining the enantioselectivity has been experimentally demonstrated. Valuable information for the reaction mechanism was accumulated.

Original languageEnglish
Pages (from-to)3452-3455
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number27
DOIs
Publication statusPublished - 2012 Jul 4
Externally publishedYes

Keywords

  • Asymmetric Michael addition
  • Bifunctional catalyst
  • C-C bond formation
  • Cyclic enone
  • Ru catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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