Date of Award
For the synthesis of certain molecules of interest in Dr. Richard Olsen's laboratory it was necessary to produce N-protected a-amino alcohols from N-protected amino acids and subsequently, after further synthesis steps, to oxidize the hydroxyl functionalities of these molecules back to carboxylic acids. A number of methods are known for the reduction of carboxylic acids to alcohols; several methods are also reported in the chemical literature for the oxidation of alcohols to carboxylic acids. The problem in finding a suitable general method, is that the amino acid side chains affect the re activity and chemistry differently in each specific case. I report a method that has been shown to be effective for the reduction and subsequent re-oxidation of a number of N-carbobenzoxy and N-tert-butyloxycarbonyl protected amino acids.
Goodfellow, Val S., "Reduction of N-Protected Amino Acids to Amino Alcohols and Subsequent Re-Oxidation to Original N-Protected Amino Acids" (1981). Undergraduate Honors Capstone Projects. 231.
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