Synthesis of highly substituted methylenecyclohexenes using new domino reactions with sultones

New methods for the synthetic elaboration of sultones with concomitant desu lfurization have been developed. Alkylation of sultones with (iodomethyl)tr imethylsilane followed by treatment of the resultant silyl compound with te trabutylammonium fluoride gave rise to sulfur-free methylenecyclohexenes. I n a more straightforward fashion, highly substituted compounds of the latte r type were readily accessible by alkylation of alpha -metallated allylic s ultones prepared either by deprotonation, radical cyclization/transmetallat ion, or conjugate 1,6-addition with (iodomethyl)magnesium chloride in a one -pot transformation. An advanced intermediate for the synthesis of several 1,10-seco-eudesmanolides was rapidly constructed using such a protocol.