Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines.
The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.
Department of Pharmacy - Drug Sciences, University of Bari, "A. Moro" Via E. Orabona 4, Bari 70125, Italy. renzo.luisi@uniba.it leonardo.degennaro@uniba.it.
Giovanna
G
Parisi
Emanuela
E
Capitanelli
Antonella
A
Pierro
Giuseppe
G
Romanazzi
Guy J
GJ
Clarkson
Leonardo
L
Degennaro
Renzo
R
Luisi
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001384:Azetidines; D057786:Peptidomimetics