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Enantioselective Synthesis and Stereoselective Rearrangements of Enol Ester Epoxides

Yuanming Zhu, Lianhe Shu, Yong Tu and Yian Shi*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA, Email:

Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem., 2001, 66, 1818-1826.

DOI: 10.1021/jo001593z

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Enol esters can be epoxidized with high enantioselectivities using a fructose-derived chiral ketone as catalyst and Oxone as oxidant. A subsequent acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. Whereas a strong acid favors retention of configuration, a weak acid favors inversion of configuration.

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proposed mechanism

Key Words

cyclohexanones, α-hydroxy ketones

ID: J42-Y2001