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

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 alpha-keto ester and an alpha-isocyanoacetate establishes an oxazoline which could be a potential chiral ligand for metalmediated catalysis, and also could be easily converted into an optically active beta-hydroxy-alpha-amino acid.Science and Technology Innovation Committee of Shenzhen Municipality [JCYJ20160226105602871]; China Postdoctoral Science Foundation [2016M590009]; Guangdong Province Special Branch Program [2014TX01R111]; Natural Science Foundation of Guangdong Province [2016A030310243]SCI(E)ARTICLE111300-13042