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Photoredox α-vinylation of α-amino acids and N-aryl amines.

ABSTRACT: A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

SUBMITTER: Noble A

PROVIDER: S-EPMC4140496 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Photoredox α-vinylation of α-amino acids and N-aryl amines.

Noble Adam A MacMillan David W C DW

Journal of the American Chemical Society 20140811 33

A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established ...[more]

PMID: 25026314

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