3-Metallated enamines XI. Transmetallation of 3-Stannylated enamines - A new method to generate 1-aminoallyllithium compounds

Article abstract of DOI:10.1055/s-1992-26292

The transmetallation of 3-stannylated enamines, 1-morpholino-3-(trialkylstannyl)cycloalk-1-enes and 3-morpholino-5-(tributylstannyl)hex-3-ene, with butyllithium is a new and general way to generate s1-aminoallyllithium compounds. Stabilization by aromatic substituents is not further necessarily as in the case of preparation by deprotonation and even the thermodynamically less stable exoamino derivatives are accessible. Therefore homoenolate-equivalents of cyclic ketones are made available. Thus, the corresponding 3-alkylated or 3-silylated cycloalkanones and alken-3-ones were prepared via the 1-morpholinoallyllithium compounds.