Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams

Org Lett. 2021 Apr 16;23(8):2895-2899. doi: 10.1021/acs.orglett.1c00536. Epub 2021 Mar 30.

Abstract

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amino Acids / chemistry*
  • Carbon Dioxide / chemistry*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Lactams / chemistry*
  • Molecular Structure
  • Sodium / chemistry
  • Styrenes / chemistry*

Substances

  • Alkenes
  • Amino Acids
  • Carboxylic Acids
  • Lactams
  • Styrenes
  • Carbon Dioxide
  • Sodium