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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Zainb on November 20, 2009, 09:44:47 AM

Title: enol esterification
Post by: Zainb on November 20, 2009, 09:44:47 AM

I try to do enol esterification of allylic ketone

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fwww.bluffton.edu%2F%7Ebergerd%2Fclasses%2FCEM222%2FHandouts%2Fketo-enol.gif&hash=67a7606f6cacb249c891d7b3837b6a00d9a7efeb)

but I did not find a suitable procedure, i try to use basic conditions like pyridine and also with activation of the acid by using shinna reagent...etc. I have mixtures from (Z) and E-ENOL ESTER with a very weak yeild.

a friend suggested using Lewis acid acid as a catalyst like BoEt3..but  i did not find any procedure in literature about that..if someone will give me a good idea, i need (E)-ENOL ESTER NOT (Z).

thanks

Title: Re: enol esterification
Post by: Jd1828 on November 20, 2009, 10:09:59 AM

cHex2B-Cl is pretty selective for E isomers

Title: Re: enol esterification
Post by: Zainb on November 20, 2009, 10:56:33 AM

Quote from: Jd1828 on November 20, 2009, 10:09:59 AM

cHex2B-Cl is pretty selective for E isomers

thanks can give me any reference if possible

Title: Re: enol esterification
Post by: Zainb on November 20, 2009, 11:22:16 AM

thanks again

cHex2B-Cl is a selective reagent for trans-enolate in aldol rections..hopefully it works with me.