Synthesis of β-lactams on solid support using Aminoacids as chiral auxiliary

Introduction An economical way to obtain optically active β-lactam derivatives is the use of amino acids as chiral auxiliaries in Staudinger reaction (Bose et al., 1985). This strategy has been used for asymmetric synthesis of bicyclic β-lactam compounds, such as 2-isocephems, from threonine (Tenneson and Belleau, 1980). In addition, β-lactams obtained by this method are useful as versatile intermediates for the preparation of α-aminoacids and derivatives and, in general, as synthon for peptide synthesis (Ojima, 1993). However, this interesting approach has been little explored in the field of solid phase organic synthesis (SPOS). In recent years SPOS methodologies have received increasing attention due to its importance as main tool leading to generation of combinatorial libraries. Undoubtedly, the interest in the synthesis of optically active β-lactam derivatives via amino acids as chiral auxiliaries, requires further investigation on the posibilities of applying solid phase chemistry. In this communication results obtained with different resins and several α-aminoacids for achieving the formation of different β-lactam derivatives will be shown.