ChemInform Abstract: Studies on the Alkylation of Dipeptide Substrates

Alkylations of anions derived from dipeptides with a glycine at the C-terminus have been investigated. A hydrocarbon sedition in the N-terminal residue does impart some asymmetric induction. The use of a chiral ester derivative provides the potential for double asymmetric induction and good selectivity. With an aspartyl residue at the N-terminus, problems were encountered due to competing side reactions. The use of an azetidinone could circumvent some of these, but the observed induction was not high.