Selective Deprotection of N-Boc-Protected tert-Butyl Ester Amino Acids by the CeCl₃ ^. 7 H₂O - NaI System in Acetonitrile

Enrico Marcantoni*, Massimo Massaccesi, Elisabetta Torregiani, Giuseppe Bartoli, Marcella Bosco, Letizia Sambri

*Dipartimento di Scienze Chimiche, via S. Agostino 1, I-62032 Camerino (MC), Italy, Email: enricomcamserv.unicam.it

E. Marcantoni, M. Massaccesi, E. Torregiani, G. Bartoli, M. Bosco, L. Sambri, J. Org. Chem, 2001, 66, 4430-4432.

DOI: 10.1021/jo010010y

Abstract

An interesting example of a selective deprotection of the tert-butyl esters in the presence of N-Boc protecting groups of several amino acids using cerium(III) chloride as a Lewis acid is reported.

see article for more examples

proposed mechanism

Key Words

tert-butyl esters, tert-butyl carbamates, carboxylic acids

ID: J42-Y2001-010

Selective Deprotection of N-Boc-Protected tert-Butyl Ester Amino Acids by the CeCl3 . 7 H2O - NaI System in Acetonitrile

Enrico Marcantoni*, Massimo Massaccesi, Elisabetta Torregiani, Giuseppe Bartoli, Marcella Bosco, Letizia Sambri

Selective Deprotection of N-Boc-Protected tert-Butyl Ester Amino Acids by the CeCl₃ ^. 7 H₂O - NaI System in Acetonitrile