Homochirality of β‐Peptides: A Significant Biomimetic Property of Unnatural Systems

Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial β‐peptides have the tendency toward homochiral diastereoselective chain elongation. Chain‐length‐dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size of the side chain drastically influenced the selectivity of the stereodiscriminative chain‐elongation reaction. It is noteworthy that water as the co‐solvent increases the selectivity. Such behavior is a novel fundamental biomimetic property of foldamers with a potential of future industrial application.