New ruthenium-based protocol for cleavage of terminal olefins to primary alcohols: improved synthesis of a bicyclic nucleoside.

Abstract

A new protocol for the oxidative cleavage of terminal alkenes to give exclusively primary alcohols in high yields is introduced. The protocol is based on RuO4-mediated dihydroxylation, NaIO4-mediated diol cleavage, and NaBH4-mediated reduction, but the introduction of a reducing step before the diol cleavage removes the formation of byproducts and improves… (More)

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