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

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...

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Bibliographic Details
Published inTetrahedron letters Vol. 53; no. 27; pp. 3452 - 3455
Main Authors Dub, Pavel A., Wang, Hui, Watanabe, Masahito, Gridnev, Ilya D., Ikariya, Takao
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 04.07.2012
Subjects
Asymmetric Michael addition
Asymmetry
Bifunctional catalyst
Bonding
Catalysis
Catalysts
chemical reactions
Conjugates
Cyclic enone
C–C bond formation
enantiomers
Ketones
Ru catalyst
Selectivity
Tetrahedrons
Cyclic enone
Ru catalyst
Bifunctional catalyst
Asymmetric Michael addition
C–C bond formation
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ISSN0040-4039
1873-3581
DOI10.1016/j.tetlet.2012.04.100

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Summary: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.
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.04.100