I am working on research. I would like to connect a conjugated aldehyde (like citral) to another ketone compound at the carbon alpha to the latter's carbonyl group. I tried to use Mukaiyama aldol reaction. I generated an enol silane from this ketone compound and then reacted with a conjugated aldehyde, but it failed. I guess that the relatively high stability of the conjugation system from conjugated aldehyde may be a reason. Can anyone suggest me another way to do the job?
I intend to do double alkylation at that carbon position and I would like to preserve an -OH or C=O group at the beta position with respect to the C=O group on the reactant conjugated aldehyde.
Dear Alan
Can you please attached the proposed synthetic scheme to clarify your question and point my answer?
Regards
Dear Alan
Can you please attached the proposed synthetic scheme to clarify your question and point my answer?
Regards
Please check the following references:
TiCl4: J. Org. Chem 2011 76(21), 8575-8587
Zn-triflate: Org. Lett. 2010, 12(4), 796-799
Chlorodicyclohexylborane: Org. Lett 2010, 12(9), 2158-2161.
J Org Chem 2010, 75(8), 2429-2444
J Org Chem 2009, 74(19), 7220-7229
Well Mr. Alan. Hope you are troubling with stability issue. Try another reaction condition. First add KOH to ketone in THF at 0 oC and stir for few minutes. Then add citral solution (THF) slowly and allow to stir the reaction mixture at 25 oC (to reflux if necessary) and monitor the reaction. This may give you positive result atleast to a certain extent.
To carry out such reactions successfully, it would help you to turn your mind to the Csp3–Csp2 cross-coupling reaction (Negishi coupling).
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