Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration.

ABSTRACT: Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B(2)(pin)(2)) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.

SUBMITTER: Burks HE 

PROVIDER: S-EPMC2747290 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature