After two semesters of Organic Chemistry, this blog entry will be my final episode of the epic journey through the long and hard days of Organic Chemistry, the nemesis of every pre-med student!
In Christina White's of the University of Illinois website for organic reactions, she presents many catalytically driven reactions that correspond directly with the topics of Chapter 26 in our Organic textbook by Smith. I picked publication #5 entitled "Poly Synthesis Through Hydrocarbon Oxidation: De Novo Synthesis of L-Galactose" by D.J. Covell, N.A Vermuellen, N.A. Labenz, and M.C. White.(1) I attempted to upload the picture but the quality of the copy was not worth publishing, the picture can be found by going to the link in the sources. They describe conditions that allow p-anisic to act as a nucleophile for the linear allylic oxidation reaction to generate compound 4 in the reaction scheme. This reaction was carried out with a Palladium catalyst in DMSO. Unlike the Heck reaction we learned about in Ch 26 of Smith, this reaction oxidized the original p-anisic acid with an ester. The Heck reaction involves the coupling of a vinyl or aryl halide with an alken to form a more highly substituted alkene with a new C-C bond.(2) The similarities between the two reactions are that both use a Pd catalyst to attach a new functional group to the compound. In this reaction, the alkene of the compound was not oxidized, alkene turning into a -OH group, until the last step. This was accomplished by asymmetric dihydroxylations (AD). In closing for the final time, by the end of two semesters of Organic Chem I can actually comprehend the actions of this reactions and how to identify each step, so I guess all that studying was good for something...
Adios Chemistry Blog world!
-KAMetz
Sources:
1. Covell, D.J et al. Polysynthesis through Hydrocarbon Oxidation: De Novo Synthesis of L-Galactose.
ACIEE.2006,45,8217-8220. http://www.scs.illinois.edu/white/index.php?p=publications (accessed May 6, 2011)
2. Janice Smith,Organic chemistry. 3rd. New York City: McGraw-Hill Companies, 2008. pg 1009
We describe conditions that allow p-anisic acid to act as a nucleophile for the linear allylic oxidation reaction to directly generate (4) with good yields (70%) and outstanding selectivities (E:Z = 97:3
Polyol Synthesis through Hydrocarbon Oxidation: De Novo Synthesis of L-Galactose".
D.J. Covell; N.A. Vermeulen; N.A. Labenz; and M.C. White.
