Synthesis of syn and anti 1,4-diols by copper-catalyzed boration of allylic epoxides

Abstract

Two sides of the same coin: Syn and anti 1,4-diols have been synthesized through the regio- and diastereoselective CuI-catalyzed boration of allylic epoxides (see scheme; pin=pinacolato, TES=triethylsilyl). In situ protection of the alcohol allows isolation of syn and anti 1,4- silyloxyboronates. Monoprotected 1,4-diols can be prepared by a one-pot addition-protection-oxidation sequence. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.