This work describes the first example of Michael addition reactions of chiral Ni (II)-complex of glycine Schiff base with 1-(1-(phenylsulfonyl)vinylsulfonyl)benzene. This approach was developed for asymmetric synthesis of 2-amino-4,4-bis (phenylsulfonyl)butanoic acid possessing various design-useful properties such as substantial steric bulk and lipophilicity. These properties are expected to provide for an improved binding to the apolar site of the various endogenous receptors. Fmoc derivative of the target amino acids ready for peptide coupling is described.
Keywords: 1(1-phenylsulfonyl)benzene; Michael additions; Ni (II)-complex of Schiff base; recyclable chiral auxiliary; tailor-made amino acids.