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Sequential Pd-Catalyzed Asymmetric Allene Diboration/α-Aminoallylation

Joshua D. Sieber and James P. Morken*

*Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email: morkenunc.edu

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

DOI: 10.1021/ja057020r (free Supporting Information)


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Abstract

Pd-catalyzed enantioselective diborations of prochiral allenes followed by allylation reactions with primary imines provide vinyl boronates which may be oxidized to give nonracemic Mannich products. Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.

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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.


Key Words

boronates, β-amino ketones, ketones, hydrogen peroxide


ID: J48-Y2006-1220