Enantiomerically Pure Intramolecular Metathathis of Double Bonds.

Abstract

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.