LETTER	Synlett 2002: 0069-0072 DOI: 10.1055/s-2002-19326
© Georg Thieme Verlag Stuttgart · New York
Synthesis of α,α-Disubstituted β-Amino Esters and Peptide Derivatives
Eduardo Alonso, Carlos del Pozo, Javier González*
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, 33071 Oviedo, Spain Fax: +34(985)103446; e-Mail: FJGF@sauron.quimica.uniovi.es;
Received 9 October 2001

Abstract

The synthesis of α,α-disubstituted β-amino esters and peptide derivatives from readily available 4-spiro-β-lactams 1 is described. The geminally disubstituted β-amino esters are obtained from the N-Boc spiro β-lactams 2 by treatment with potassium cyanide in methanol. Alternatively, the use of spiro β-lactams 2 as acylating agents of the amino group of C-protected amino acids, allowed its direct incorporation into a peptidic chain.

Key words

amino acids - lactams - peptides - ring opening - spiro compounds