Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar

An effective method to diastereoselectively synthesize enantioenriched propargylic fluorides was developed via SN1 type reaction of DAST participated dehydroxy-fluorination of diastereomeric propargylic alcohol cobalt–carbonyl complexes. A serious of propargylic fluorides can be prepared by this approach in good yields with moderate to high diastereoselectivities. To demonstrate the application of this approach in synthesis, monofluorinated sugar 12, an important and versatile building block, was prepared in an efficient manner.