Regioselective Cleavage of Phenyl- or Alkyl-Substituted Epoxides with Al-Fluorodiisobutylalane

摘要

In the previous communication, we reported that boron triisopropoxide attacked aryl epoxides slowly but regio-selectively to produce the anti-Markovnikov ring-opened reduction products in the Meerwein-Ponndorf-Verley (MPV) type reduction procedure. In the course of our successive efforts to devise new unique MPV type reagents, we found Al-fluorodiisobutylalane (DIBAF), a new MPV type reagent, reacts readily with both aromatic and aliphatic epoxides to produce the corresponding alcohols in an essentially perfect regioselectivity. This paper described such a regioselective MPV type reduction of epoxides.