Enantioselective Synthesis of Acyclic Stereotriads Featuring Fluorinated Tetrasubstituted Stereocenters
Résumé
A sequence of two unprecedented steps is described to build acyclic stereotriads bearing a fluorinated tetrasubstituted stereocenter. The sequence combines a highly diastereoselective aldol-Tishchenko reaction from readily available starting materials with an acylative double organocatalyzed kinetic resolution (DoCKR) providing enantioenriched products. This method is practically simple, general, and flexible affording different diastereomers depending on the initial substrates. A mechanistic study supports the observed stereochemistry of fluorinated products.