2021Organic LettersRequires access

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

Cong Zhou, Miao Li, Jianwei Sun, Jiang Cheng, Song Sun

Open publisher page 63 citations

Abstract

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO 2 has been developed to synthesize a series of α,α -disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO 2 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 CO 2 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 CO 2 reutilization in decarboxylation reactions.

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What this paper is about

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO 2 has been developed to synthesize a series of α,α -disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO 2 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 CO 2 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 CO 2 reutilization in decarboxylation reactions.

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Available abstract

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO 2 has been developed to synthesize a series of α,α -disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO 2 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 CO 2 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 CO 2 reutilization in decarboxylation reactions.

Key concepts: Carboxylation, Decarboxylation, Chemistry, Regioselectivity, Olefin fiber, Catalysis, Amino acid, Carbonylation

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Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams — Research Paper | ScholarLens