Michael addition reactions of chiral glycine Schiff base Ni (II)‐complex with 1‐(1‐phenylsulfonyl)benzene

• Published in: Chirality (New York, N.Y.) Vol. 32; no. 6; pp. 885 - 893
• Main Authors: Nagaoka, Keita, Mei, Haibo, Guo, Yunjie, Han, Jianlin, Konno, Hiroyuki, Moriwaki, Hiroki, Soloshonok, Vadim A.
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01-06-2020
• Subjects: 1(1‐phenylsulfonyl)benzene; Amino acids; Asymmetric synthesis; Benzene; Butyric acid; Glycine; Hydrocarbons; Imines; Lipophilicity; Michael additions; Ni (II)‐complex of Schiff base; recyclable chiral auxiliary; tailor‐made amino acids; 1(1-phenylsulfonyl)benzene; recyclable chiral auxiliary; tailor-made amino acids; Michael additions; Ni (II)-complex of Schiff base
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.23203

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.