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Cationic [2,6-Bis(2‘-oxazolinyl)phenyl]palladium(II) Complexes:  Catalysts for the Asymmetric Michael Reaction

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Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff CF10 3TB, U.K.
Cite this: Organometallics 2000, 19, 7, 1282–1291
Publication Date (Web):March 4, 2000
Copyright © 2000 American Chemical Society

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    Reaction of 1,3-dicyanobenzene with β-amino alcohols (S)-H2NCHRCH2OH (R = iPr, iBu, tBu, CH2Cy, CH2Ph) and (R)-H2NCHPhCH2OH gave new 1,3-bis(2‘-oxazolinyl)benzenes (30−51%). These, together with 1,3-bis(4‘,4‘-dimethyl-2‘-oxazolinyl)benzene, were treated with LDA/TMEDA followed by the addition of PdBr2(1,5-COD) to give [2,6-bis(2‘-oxazolinyl)phenyl]palladium(II) bromide complexes (21−41%). In two cases no complexes were obtained (R = Ph, CH2Ph) due to ring opening of the oxazolines by LDA/TMEDA. Treatment of the palladium complexes with AgBF4, AgOTf, or AgSbF6 in wet CH2Cl2 provided a series of cationic [2,6-bis(2‘-oxazolinyl)phenyl]palladium complexes (28−87%) containing water coordinated to palladium, as established by an X-ray crystal structure analysis of (S,S)-[2,6-bis(4‘-isopropyl-2‘-oxazolinyl)phenyl]aquopalladium(II) trifluoromethanesulfonate. All of the cationic complexes proved to be efficient catalysts for the Michael reaction between α-cyanocarboxylates and methyl vinyl ketone and between acrylonitrile and activated Michael donors. Selectivities of up to 34% ee were obtained for the formation of (R)-ethyl 2-cyano-2-methyl-5-oxohexanoate.

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    Text giving full characterization data for 16a2, 16a3, 16b1, 13g, 14g, 18, and 12 and details of the X-ray structure determination of 16b2. This material is available free of charge via the Internet at

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