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J Am Chem Soc. 2014 Aug 20;136(33):11602-5. doi: 10.1021/ja506094d. Epub 2014 Aug 11.

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

Author information

1
Merck Center for Catalysis at Princeton University , Princeton, New Jersey 08544, United States.

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.

PMID:
25026314
PMCID:
PMC4140496
DOI:
10.1021/ja506094d
[Indexed for MEDLINE]
Free PMC Article

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