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Development, Mechanism, and Scope of the Palladium-Catalyzed Enantioselective Allene Diboration

Heather E. Burks, Shubin Liu and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: morkenbc.edu

H. E. Burks, S. Liu, J. P. Morken, J. Am. Chem. Soc., 2007, 129, 8766-8773.

DOI: 10.1021/ja070572k


Abstract

In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity with a range of aromatic and aliphatic allenes. A mechanism is proposed based on isotopic-labeling experiments, stereodifferentiating reactions, kinetic analysis, and computational experiments.

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Palladium-Catalyzed Enantioselective Diboration of Prochiral Allenes

N. F. Pelz, A. R. Woodward, H. E. Burks, J. D. Sieber, J. P. Morken, J. Am. Chem. Soc., 2004, 126, 16328-16329.

Sequential Pd-Catalyzed Asymmetric Allene Diboration/α-Aminoallylation

J. D. Sieber, J. P. Morken, J. Am. Chem. Soc., 2006, 128, 74-75.


Key Words

boronates


ID: J48-Y2007-2310