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