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The stereochemistry of the cyclization of 4-(t-butyldimethyl)siloxy-5-hexenyllithium, generated from the corresponding iodide by low - temperature lithium - iodine exchange, has been studied. The results of these studies demonstrate that the ring closure, which is cis-selective in all of the solvent systems investigated, is accompanied by a facile (1,4)-C→O migration of the silyl group in cis-(2-(t-butyldimethylsiloxy)cyclopentylmethyl)lithium (a retro-(1,4)-Brook rearrangement). The factors responsible for the cis-selectivity observed in these cyclizations are discussed.

arkivoc

Stereochemistry of the cyclization of 4-(t-butyldimethyl)siloxy-5-hexenyllithium: cis-selelective ring-closure accompanied by retro-[1,4]-Brook rearrangement