An asymmetric biomimetic aldol reaction of glycinate with aliphatic aldehydes for efficient synthesis of chiral β-hydroxy-α-amino acid esters

Abstract

In biological systems, enzyme-catalyzed processes are efficient and environmentally friendly ways for the transformations of various substances. Biomimetic processes can provide straightforward strategies for the synthesis of target molecules. The asymmetric biomimetic aldol reaction of glycinate is a highly efficient method for the synthesis of chemically and biologically important chiral β-hydroxy-α-amino acid esters. Herein, we developed an asymmetric aldol reaction of glycinate with aliphatic aldehydes using chiral N-quaternized pyridoxal as the catalyst, affording a variety of chiral β-hydroxy-α-amino acid esters in 20–91% yields, with up to >20 : 1 dr and up to 99% ee.