Modular asymmetric synthesis of 1,2-diols by single-pot allene diboration/hydroboration/cross-coupling.
Chiral allyl vinyl boronates are generated by catalytic enantioselective diboration of prochiral allenes. They may then be reacted, in situ, with a hydroborating reagent to form a novel triboron intermediate. The least hindered and most reactive C-B bond then participates in cross-coupling wherein the coupling is brought about by the same catalyst as that which catalyzed the diboration reaction. The remaining C-B bonds are then oxidized in the reaction workup, thereby allowing for the modular synthesis of chiral diols in a concise single-pot fashion.
Pelz
Nicholas F
NF
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Morken
James P
JP
D000466:Alkadienes / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism
D000466:Alkadienes; D001896:Boron Compounds; C025947:propadiene