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Dual catalytic decarboxylative allylations of α-amino acids and their divergent mechanisms
Lang, Simon Bouyea O'Nele, Kathryn M. Douglas, Justin T. Tunge, Jon A.
Lang, Simon Bouyea
O'Nele, Kathryn M.
Douglas, Justin T.
Tunge, Jon A.
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Abstract
The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
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This is the peer reviewed version of the following article: Lang, S. B., O'Nele, K. M., Douglas, J. T. and Tunge, J. A. (2015), Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms. Chem. Eur. J., 21: 18589–18593. doi:10.1002/chem.201503644, which has been published in final form at http://doi.org/10.1002/chem.201503644. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
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2015-12-14
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Wiley
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Lang, S. B., O'Nele, K. M., Douglas, J. T. and Tunge, J. A. (2015), Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms. Chem. Eur. J., 21: 18589–18593. doi:10.1002/chem.201503644