Recent Advances in the Catalytic Asymmetric Synthesis of β2‐ and β2,2‐Amino Acids

• Published in: European journal of organic chemistry 2020-05, Vol.2020 (16), p.2350-2361
• Main Authors: Noda, Hidetoshi, Shibasaki, Masakatsu
• Format: Article
• Language: English
• Subjects: Acrylates; Amino acids; Asymmetric catalysis; Asymmetry; Carbonyl compounds; Carbonyls; Chemical synthesis; Enantiomers; Homogeneous catalysis; Natural products; Peptidomimetics; Synthetic methods
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901596

The importance of β‐amino acids for peptidomimetics and their presence in numerous natural products and pharmaceuticals make the development of the corresponding synthetic procedures a task of high practical significance. Herein, we focus on the recent developments in the catalytic asymmetric synthesis of β2‐ and β2,2‐amino acids. The examples are arranged according to strategic bond disconnections. Despite the abundance of feasible approaches, only a handful of reaction types can effectively furnish β2‐ and β2,2‐amino acid derivatives with sufficient enantioselectivity suitable for peptide applications. These include asymmetric hydrogenation or conjugate addition of acrylates, α‐functionalization of β‐amino acid enolate precursors, and aminomethylation of carbonyl compounds. Hence, future research directions are discussed considering these literature precedents. Recent developments in the catalytic asymmetric synthesis of β2‐ and β2,2‐amino acids are summarized according to strategic bond disconnections. Literature search reveals that only a handful of reaction types has been succeeded in delivering β‐amino acid derivatives in sufficient enantioselectivity suitable for peptide applications.