Tetrahedron Letters p. 7823 - 7826 (1992)
Update date:2022-08-25
Topics:
Tang
Kennedy
2-Hydroxyethyl enol ethers react with Re2O7 to produce 2-hydroxyketals. Where homochiral starting enol ethers are employed, greater than 99:1 diastereoselectivities are obtained. The stereocontrol is rationalized by invoking a transition state that approximates the geometry of a metallaoxetane. Finally, homochiral ketals are themselves oxidized to provide 2-hydroxyketals with high diastereoselectivity.
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