Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction
- 27 November 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (1) , 131-133
- https://doi.org/10.1021/ol036219a
Abstract
Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C−B bond participates in cross-coupling. The remaining C−B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.Keywords
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