Abstract
Stereoselective amino-cycloaddition of alkenylamines is one of the most important approaches for the stereoselective construction of nitrogen hetero-alicycles, which form the skeletons of several bio-logically active natural products and related compounds. We recently developed the intramolecular substitution of an allylic alcohol by a heteroatom using a palladium (II) catalyst without activation of the allylic alcohol. This review describes the stereoselective cyclization of the optically active urethanes and oxazolidinones containing allyl alcohol moiety using bis (acetonitrile) palladium (II) chloride leading to the 2-functionalized 5-hydroxypiperidine, the trans-2, 5-disubstituted pyrrolidine, and the trans -2, 6-piperidine, respectively. The stereoselective construction of different stereoisomers from similar precursors by changing transition metals (a palladium (II) catalyst → a silver salt) is also described.
The cyclo-adducts obtained were proved to be useful chiral building blocks by their conversion into (+) -coniine, (-) -5-hydroxysedamine, (-) -bulgecinine, (+) -prosopinine, and a prospective synthetic intermediate of (+) -palustrine, respectively.
