α-Amino acid chlorides are reactive coupling agents in amide (peptide) formation. The
Vilsmeier reagent ((chloromethylene)dimethylammonium chloride) offers a convenient way to prepare
α-amino acid chlorides for peptide synthesis. Its use with N-trifluoracetyl (TFA)-protected isoleucine
and allo-isoleucine is described. The 1H-NMR of the α-proton signal offers a convenient way to monitor
the chirality retention in the acid chloride forming reaction and subsequent Friedel-Crafts acylation
of arenes which result in α-amino acid aryl-ketone with no loss of chirality.
Keywords: Vilsmeier reagent, α-Amino acid chloride, Friedel-Crafts acylation, α-amino acid, α-amino arylketone, racemization.
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