4.8 Article

Photochemical single-step synthesis of β-amino acid derivatives from alkenes and (hetero)arenes

Journal

NATURE CHEMISTRY
Volume 14, Issue 10, Pages 1174-+

Publisher

NATURE PORTFOLIO
DOI: 10.1038/s41557-022-01008-w

Keywords

-

Funding

  1. Alexander von Humboldt Foundation
  2. Deutsche Forschungsgemeinschaft [SFB 858]
  3. Institute for Basic Science in the Republic of Korea [IBS-R010-D1]

Ask authors/readers for more resources

Beta-amino acids are important components in many biologically active molecules, drugs, and natural products. A metal-free, energy-transfer enabled intermolecular aminocarboxylation reaction has been developed for the single-step installation of amine and ester functionalities into alkenes or (hetero)arenes. This mild method shows broad substrate scope, good tolerance of sensitive functional groups, and provides a general and practical access to beta-amino acid derivatives.
beta-Amino acids are frequently found as important components in numerous biologically active molecules, drugs and natural products. In particular, they are broadly utilized in the construction of bioactive peptides and peptidomimetics, thanks to their increased metabolic stability. Despite the number of methodologies established for the preparation of beta-amino acid derivatives, the majority of these methods require metal-mediated multistep manipulations of prefunctionalized substrates. Here we disclose a metal-free, energy-transfer enabled highly regioselective intermolecular aminocarboxylation reaction for the single-step installation of both amine and ester functionalities into alkenes or (hetero)arenes. A bifunctional oxime oxalate ester was developed to simultaneously generate C-centred ester and N-centred iminyl radicals. This mild method features a remarkably broad substrate scope (up to 140 examples) and excellent tolerance of sensitive functional groups, and substrates that range from the simplest ethylene to complex (hetero)arenes can participate in the reaction, thus offering a general and practical access to beta-amino acid derivatives.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available