In tetrafluoroborate based ionic liquids fair yields and enantiomeric excesses up to 91% were obtained in the Michael addition of ethyl cyclohexanone-2-carboxylate to methyl vinyl ketone, using (R,R)-trans-1,2-diaminocyclohexane as chiral auxiliary (37% mol/mol with respect to the donor). The presence of catalytic amounts of metal sources [Ni(OAc)(2)center dot 4H(2)O, Co(acac)(2), FeCl(3)center dot 6H(2)O, LaCl3, Cu(OAc)(2)center dot H2O] did not improve the activity, and, in some instances, caused a drop of enantioselectivity. Reactions carried out in the absence of any metal and with a Michael donor/diamine molar ratio of 20 allowed us to ascertain that the reaction can be performed catalytically.

Asymmetric Michael addition promoted by (R,R)-trans-1,2-diaminocyclohexane in ionic liquids / Gallo, Vito; Giardina-Papa, Daniela; Mastrorilli, Piero; Nobile, Cosimo Francesco; Suranna, Gian Paolo; Wang, Yaquan. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - STAMPA. - 690:15(2005), pp. 3535-3539. [10.1016/j.jorganchem.2005.02.019]

Asymmetric Michael addition promoted by (R,R)-trans-1,2-diaminocyclohexane in ionic liquids

Vito Gallo;Piero Mastrorilli;Cosimo Francesco Nobile;Gian Paolo Suranna;
2005-01-01

Abstract

In tetrafluoroborate based ionic liquids fair yields and enantiomeric excesses up to 91% were obtained in the Michael addition of ethyl cyclohexanone-2-carboxylate to methyl vinyl ketone, using (R,R)-trans-1,2-diaminocyclohexane as chiral auxiliary (37% mol/mol with respect to the donor). The presence of catalytic amounts of metal sources [Ni(OAc)(2)center dot 4H(2)O, Co(acac)(2), FeCl(3)center dot 6H(2)O, LaCl3, Cu(OAc)(2)center dot H2O] did not improve the activity, and, in some instances, caused a drop of enantioselectivity. Reactions carried out in the absence of any metal and with a Michael donor/diamine molar ratio of 20 allowed us to ascertain that the reaction can be performed catalytically.
2005
Asymmetric Michael addition promoted by (R,R)-trans-1,2-diaminocyclohexane in ionic liquids / Gallo, Vito; Giardina-Papa, Daniela; Mastrorilli, Piero; Nobile, Cosimo Francesco; Suranna, Gian Paolo; Wang, Yaquan. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - STAMPA. - 690:15(2005), pp. 3535-3539. [10.1016/j.jorganchem.2005.02.019]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11589/300
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