• From left: F. Wang, J. Chen, Y. Huang (Peking University, P. R. of China)

     

Organocatalytic Synthesis of non-Racemic Oxazolines from Isocyanoacetate and α-Keto Esters

Jiean Chen und Yong Huang berichten über die organokatalytische Synthese von nicht-racemischen Oxazolinen.

Synthesis of Optically Active Oxazolines by an Organocatalytic Isocyanoacetate Aldol Reaction with α-Keto Esters: F. Wang, J. Chen, Y. Huang
Synlett 2017, 28, DOI: 10.1055/s-0036-1588718

Five-membered nitrogen-containing heterocycles trigger remarkable interest in drug discovery, but there are still significant synthetic challenges connected with the preparation of some of these molecules, especially if chiral and non-racemic. The use of [3+2] cycloaddition reactions represents a very useful tool for the synthesis of azoles, including oxazolines. The group of Professor Yong Huang from Peking University (P. R. of China) has recently published a versatile stereocontrolled entry to chiral oxazolines, using a bifunctional organocatalyst and isocyanoacetate as nucleophile in aldol-type reactions.

  • Synthesis of oxazolines with a quaternary chiral center

     

Professor Chen said: “This work demonstrates that enantioselective aldol reactions of keto esters enable access to amino acid derivatives with a quaternary chiral center.”

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