Protection of the indole ring of tryptophan by the benzyloxycarbonyl group is achieved by acylation with p-nitrophenyl benzyl carbonate in the presence of unsolvated fluoride anion, generated by crown ethers.
M. Chorev and Y. S. Klausner, J. Chem. Soc., Chem. Commun., 1976, 596a DOI: 10.1039/C3976000596A
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