Tetrahedron Letters p. 685 - 688 (1998)
Update date:2022-08-05
Topics:
Rutherford, Alistair P.
Gibb, Cameron S.
Hartley, Richard C.
We have developed a stereoselective route to β-hydroxycyclohexanones using the aldol reaction, the Takai alkylidenation, a novel anionic oxy-Cope rearrangement of acyclic enol ethers and an intramolecular aldol reaction. The stereoselectivity of the acid-induced, 6-(enolendo)-exo-trig, intramolecular, aldol reaction between an aldehyde and an enol ether has been investigated. The strong preference for an axial hydroxyl in the β-hydroxycyclohexanone products is explained in terms of an electrostatic interaction in the oxonium ion intermediate.
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