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Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

Adam Noble and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

A. Noble, D. W. C. MacMillan, J. Am. Chem. Soc., 2014, 136, 11602-11605.

DOI: 10.1021/ja506094d (free Supporting Information)


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Abstract

The union of vinyl sulfones with photoredox-generated α-amino radicals enables direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, to provide allylic amines of broad diversity in high yield and with excellent olefin geometry control. The utility of this reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

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Decarboxylative Hydroalkylation of Alkynes

N. A. Till, R. T. Smith, D. W. C. MacMillan, J. Am. Chem. Soc., 2018, 140, 5701-5705.


Key Words

pyrrolidines, allylic amines


ID: J48-Y2014