Our final blog post for the semester was to go to Christina White's (U.Illinois) page and find a publication that interests us and talk about it. After looking for some time, I came across this publication on the Synthesis of Complex Allylic Esters via C-H Oxidation vs. C-C Bond Formation. The article talks about commonly used reaction methods to produce alylic esters. These methods are Horner-Wadsworth-Emmons (HWE), Linear Allylic Oxidation (LAO) and Grubbs Cross Metathesis (I apologize for not having any reaction schemes or diagrams on this blog because I could not download the image from the site as a picture. But you can follow the link below to take a look at it). What I found interesting yet a bit difficult to understand was the actual reaction procedures that were carried out. The procedure used one common starting material and used two different routes, Olefination and Oxidation, to come to one common product. Each route had different yields of the product.
What I found more interesting was The Horner-Wadsworth-Emmons (HWE) reaction, so I just went ahead and did a little bit of research on it.
The Horner-Wadsworth-Emmons reaction (HWE) is a chemical reaction of stabilized phosphonate carbanions with aldehydes and ketones to produce E-alkenes. It is a stereoselective reaction where the stereochemistry is set by steric approach control.
The HWE reaction employs similar mechanism to that of the Wittig reaction which we learned not too long ago.
Sources cited:
1.Vermeulen, Nicolass A. et al. Synthesis of Complex Allylic Esters via C-H Oxidation vs C-C Bond Formation. JACS, 2010, 132, 11323. http://www.scs.illinois.edu/white/index.php?p=publications
2. http://www.organic-chemistry.org/namedreactions/wittig-horner-reaction.shtm
3.
http://en.wikipedia.org/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction
