Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 19, Pages 6176-6179Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03477
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- University of North Carolina at Chapel Hill
- Eli Lilly New Faculty Award
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The first catalytic enantio- and diastereoselective synthesis of 1;2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., arid 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the alpha-boryl component.
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