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Surprisingly, during asymmetric reduction of my benzylic ketone (prochiral ) by Itsuno corey reduction, the vinylic (ortho positon)protons are disappearing as per the NMR spectra. This would normally imply hydroboration, but I am not using any NaOH/H2O2 to quench my reaction mixture, and using MeOH instead.

Any ideas on what might be going on here?

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@lost_gemeng, you might get a better response by including a graphical reaction scheme in the body of your quesiton. You can insert images into your question by hosting them on a server such as imgur.com . You can edit your question at any time. – Rich Apodaca Jun 21 at 16:07

1 Answer

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You may well be adding BH3 to the double bond, especialy in the ortho position, quenching with methanol would then give B(OMe)3. I shall look in Scifinder when I get back to work.

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