Highly Diastereoselective and Enantioselective Synthesis of α-Hydroxy β-Amino Acid Derivatives: Lewis Base Catalyzed Hydrosilylation of α-Acetoxy β-Enamino Esters

摘要

Chiral α-hydroxy β-amino acid moieties are important structural components in a wide variety of biologically active compounds as well as natural products, of which the side chains of Taxol and its analogues are the most famous examples. Consequently, the synthesis of chiral α-hydroxy β-amino acid derivatives has attracted considerable attention. Some syntheses include the Sharpless asymmetric aminohydroxylation, asymmetric dihydroxylation, ring opening of chiral epoxides, asymmetric nitroaldol reactions asymmetric Mannich reaction, asymmetric 1,3-dipolar cycloaddition, and other transformations. Among the successful strategies developed for obtaining optically active α-hydroxy β-amino acid derivatives, those that lead to substrates containing certain functional groups are of great significance. Accordingly, it can be reasoned that direct asymmetric reduction of the corresponding C=N double bond in substrates would be the most straightforward way to construct chiral α-hydroxy β-amino acid derivatives. However, to the best of our knowledge, the research on the above-mentioned reaction has not yet been reported.