Lithium naphthalenide induced reductive cleavage of α,β-epoxy ketones: an efficient procedure for the preparation of β-hydroxy ketones

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Renata Jankowska, Hsing-Jang Liu and George L. Mhehe


Abstract

Lithium naphthalenide presents itself as a mild and efficient reagent for the cleavage of α,β-epoxy ketones to give the corresponding β-hydroxy ketones in good yields.


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