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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:

B. Potter, A. A. Szymaniak, E. K. Edelstein, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 17918-17921.

DOI: 10.1021/ja510266x (free Supporting Information)

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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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A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

C. Sun, B. Potter, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 6534-6537.

Key Words

Suzuki coupling, vinylation, allylboronates

ID: J48-Y2014