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Synthesis of Optically Active Oxazolines by an Organocatalytic Isocyanoacetate Aldol Reaction with α-Keto Esters

Fei Wang, Jiean Chen* and Yong Huang*, Synlett 2017, DOI: 10.1055/s-0036-1588718（Invited Synlett Cluster）

An enantioselective [3+2] cyclization is reported for the construction of a chiral oxazoline skeleton in moderate yield and up to 97% ee. The reactivity and stereochemical discrimination originate from the noncovalent interaction and orientation of a bifunctional catalyst. The novel combination of an α-keto ester and an α-isocyanoacetate establishes an oxazoline which could be a potential chiral ligand for metalmediated catalysis, and also could be easily converted into an optically active β-hydroxy-α-amino acid.