Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides
Bowman Potter, Adam A. Szymaniak, Emma K. Edelstein and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston
College, Chestnut Hill, Massachusetts 02467, United States, Email: morken
bc.edu
B. Potter, A. A. Szymaniak, E. K. Edelstein, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 17918-17921.
DOI: 10.1021/ja510266x
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Abstract
Catalyzed by a chiral palladium complex, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate allyl boronates with high levels of enantioselectivity. Oxidation of these allyl boronates with hydrogen peroxide provides secondary allylic alcohols, whereas nitrosobenzene as oxidant furnishes nonracemic tertiary allylic alcohols.
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C. Sun, B. Potter, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 6534-6537.
Key Words
Suzuki coupling, vinylation, allylboronates
ID: J48-Y2014
