Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins

Keisuke Asano and Seijiro Matsubara present a selective cycloetherification via DKR of chiral cyanohydrins.

Enantioselective synthetic approaches to six-membered oxacycles are in high demand to enable the discovery of new potential therapeutic agents and bioactive molecules. However, the lack of a simple robust method for such enantioselective syntheses has limited their development. In particular, as the enantio- and diastereoselective construction of multiple stereocenters in a single operation often poses a formidable challenge, it remains desirable to develop a concise efficient method for the asymmetric installation of more than one chiral center in tetrahydropyrans.

Recently, the group of Professors Seijiro Matsubara and Keisuke Asano at Kyoto University (Japan) discovered a concise organocatalytic cycloetherification for the highly enantio- and diastereoselective synthesis of tetrahydropyrans, involving simultaneous construction of two stereogenic centers, one of which is fully substituted. This method involves dynamic kinetic resolution of reversibly generated chiral cyanohydrins.


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