The above is one of the final reactions in the synthesis of an enantiospecifically labeled fatty acid. It involves a reduction with Lindlar’s Catalyst in the presence of deuterium, an isotope of hydrogen. Lindlar’s Catalyst (powdered barium sulfate coated with Pd, poisoned with quinoline) converts an alkyne to a cis-alkene, as seen in the reaction above. The article I looked at focused on pheromone biosynthesis in S. isatideus and the role stereochemistry played.
The picture above shows a few of the steps in the creation of amphetamines. In these steps, tosyl chloride is added to (2,5-dimethoxyl-4-methylphenyl)-2-propanol to create the tosylate. After this step, the reaction can proceed in one of two ways. If the chirality of the amphetamine is not important, ammonia is added to the tosylate to give 2,5-dimethoxy-4-methylamphetamine. This reaction has an 80% yield, but has a racemic mixture of products because it is thought to be an SN1 reaction. If the chirality is important, the tosylate is converted into an azide with sodium azide, then hydrogenated using a paladium catalyst to form 2,5-dimethoxy-4-methylamphetamine. Forming the amphetamine using this method gives a final yield of about 77%. The chirality of the original alcohol is inverted by the tosylation, so reacting an (S)-alcohol with the tosyl-azide-hydrogen sequence would give an (R)-amphetamine, and vice versa.
Organic molecules contain carbon
Alcohol
hydrocarbon with a hydrogen replaced by “OH”.
Acid
hydrocarbon with a hydrogen replaced by a carboxyl “COOH”.
COOH -> COO- + H+
Amine
hydrocarbon with a hydrogen replaced by an amine “NH2″. Basic- accepts protons. NH2 + H+ -> NH3+
Phosphate
addition of -PO4= (switch)
Amino Acid
hydrocarbon with amino and carboxyl groups
