Tetrahedron Letters p. 4631 - 4634 (1998)
Update date:2022-08-04
Topics:
Tester, Richland W.
West
Cyclic acetals and ketals with pendant diazoketones rearranged to O- bridged medium ring in the presence of catalytic Rh2(OAc)4 or Cu(hfacac)2. This process proceeds via fused bicyclic oxonium ylides which undergo [1,2]- shift reactions. The observation of efficient migration by alkyl substituted carbons lacking any conjugating groups is especially notable. Overall, this chemistry furnishes functionalized medium ring ethers in a few steps from simple precursors.
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