Abstract

An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

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