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Palladium-Catalyzed Enantioselective Diboration of Prochiral Allenes

Nicholas F. Pelz, Angela R. Woodward, Heather E. Burks, Joshua D. Sieber and James P. Morken*

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

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

DOI: 10.1021/ja044167u (free Supporting Information)


Abstract

Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is accelerated in the presence of Lewis basic ligands. A chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86-92% ee.

see article for more examples



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

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

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-Y2004-1940