New simple and recyclable O-acylation serine derivatives as highly enantioselective catalysts for the large-scale asymmetric direct aldol reactions in the presence of water

New classes of O-acylation serine derived organocatalysts have been synthesized one-step by rational combination of serine with acyl chlorides at room temperature in trifluoroacetic acid. No protecting groups or chromatographic techniques are involved in any of the procedures, and certain combined serine-surfactant organocatalysts mediate the direct aldol reactions of ketones with a series of aromatic aldehydes to provide the aldol products in high yields (up to 99%) and enantioselectivities (up to 99% ee). The catalyst 1b can be easily recovered and reused, and without significant decrease of enantioselectivity was observed for five cycles. This novel catalyst can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry.

Graphical abstractNew classes of O-acylation serine derived organocatalysts have been synthesized one-step by rational combination of serine with acyl chlorides at room temperature in trifluoroacetic acid. No protecting groups or chromatographic techniques are involved in any of the procedures, and certain combined serine-surfactant organocatalysts mediate the direct aldol reactions of ketones with a series of aromatic aldehydes to provide the aldol products in high yields (up to 99%) and enantioselectivities (up to 99% ee). The catalyst 1b can be easily recovered and reused, and without significant decrease of enantioselectivity was observed for five cycles. This novel catalyst can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry.Download full-size image