Synthetic elaboration of the side chain of (R)-2,2-dimethy-3-t-butoxycarbonyl-4-ethenyl-oxazolidine: a new regio- and stereoselective strategy to delta-functionalized gamma-amino alcohols

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 provided the corresponding stannylated (E)-ethenyloxazolidine , 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