Journal of Organic Chemistry p. 2460 - 2468 (1980)
Update date:2022-07-30
Topics:
Wilson, Stephen R.
Misra, Raj N.
Georgiadis, Gregory M.
The allylic alcohols formed from 1,2-addition of 2-lithio-1,3-dithianes to α,β-unsaturated ketones have been shown to undergo <1,3> rearrangement to afford their respective Michael-addition products upon treatment with KH in HMPA/THF in some cases.The major side reaction and in some instances the sole reaction pathway was fragmentation.The rearrangement was applied to a two-carbon macrocyclic ring-expansion strategy which is illustrated in a synthesis of DL-muscone, a 15-membered-ring ketone, from cyclotridecanone.Attempts to induce a similar rearrangement by replacing the 1,3-dithiane group with a thiophenyl or 1,3-dithiolane group proved unsuccessful.
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