Re: ORGLIST: Conjugate Reduction and Side Reactions

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From: bin hu (hu_bin1976$##$hotmail.com)
Date: Thu Nov 15 2007 - 00:34:50 EST


 
Dear_Jeremy:
 
You can try the regular method (H2/Pd-C/ethaol), but with addition of a little 2 N HCl
(ethanol: HCl/V: V= 10:1), the reaction conduct under 50 psi/50~60 degree.
 
may you have good luck!
 
Bin > To: everybody$##$orglist.net> From: carr030$##$bama.ua.edu> Date: Thu, 25 Oct 2007 09:59:36 -0500> Subject: ORGLIST: Conjugate Reduction and Side Reactions> > I'm currently trying to do a conjugate reduction on methyl (E)-5- > phenyl-2-pentenoate to give the corresponding aliphatic ester. There > are numerous examples of this in the literature, but they either > feature enantioselective methods (using a chiral ligand) or > ridiculously air-sensitive compounds (Stryker's reagent). I found a > recent reference suggesting that Phebox Rh(I) and triethoxysilane in > 60 C toluene will do the desired transformation in an hour. I've > substituted Wilkinson's catalyst and got a mixture of products; > eventually, I found the desired product, but it looks like roughly > 50% conversion.> > Has anyone had success doing a similar reaction? Will Wilkinson's > contribute to side reactions?> > Does anyone know about reacting the generated silyl enol ether with a > bromonium source to trap th
 e corresponding alpha-bromide?> > Thanks,> > -Jeremy> _______________________________________________> ORGLIST - Organic Chemistry Mailing List> Website / Archive / FAQ: http://www.orglist.net> To post a message (TO EVERYBODY) send to everybody$##$orglist.net> To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address
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