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Exploring Substrate Scope of Shi-Type Epoxidations

Natalia Nieto, Ian J. Munslow, Héctor Fernández-Pérez, Anton Vidal-Ferran*

*Institute of Chemical Research of Catalonia (ICIQ), Avgda. Països Catalans 16, 43007 Tarragona, Spain, Email:

N. Nieto, I. J. Munslow, H. Fernández-Pérez, A. Vidal-Ferran, Synlett, 2008, 2856-2858.

DOI: 10.1055/s-0028-1083545 (free Supporting Information)


Enantioselective epoxidations of alkenes were achieved using a Shi-type carbohydrate-derived hydrate and Oxone. The chiral platform provided by the catalyst tolerates a wide range of substituents providing high yields and enantioselectivities. However, styrene derivatives were only converted with poor selectivities.

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Key Words

Epoxides, Organocatalysis, Oxone, Shi Epoxidation

ID: J60-Y2008-3500