INTRAMOLECULAR CYCLIZATIONS OF ORGANOMETALLIC COMPOUNDS IV. HETEROATOM INFLUENCE ON CYCLIZATIONS OF ORGANOLITHIUM COMPOUNDS

Article abstract of DOI:10.1016/S0040-4039(01)82995-6

Alkoxyl groups in alkenyllithiums can influence the stereochemistry of cyclization.The presence of n-butyllithium increases the stereoselectivity such that only one stereochemistry results; the presence of TMEDA negates the heteroatom's influence so that only the other stereochemistry results.Yields are 33percent to 44percent.