Enantiomerically Pure Intramolecular Metathathis of Double Bonds.
Synthesis of enantiomerically pure and biologically important molecules is one of the most challenging problems facing organic chemists today. Through a series of enzymatic and organometallic catalyses we are able to make a number of enantiomerically pure compounds which can later be fashioned into drugs. Using the enzyme oxynitrilase various enantiomerically pure cyanohydrins are synthesized from their corresponding a,b-unsaturated aldehydes. The cyanohydrin of crotonaldehyde is then made into its corresponding ester. The ester can then be converted into an allyl amide and then the Grubb's can catalyze a ring closing metathesis reaction. Enantiopurity is conserved in both cases because the chiral carbons are untouched in each and every reaction after it is made in the cyanohydrin reaction.
Papazian, Jason, "Enantiomerically Pure Intramolecular Metathathis of Double Bonds." (2003). URC Student Scholarship.
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