Visible-light-mediated catalytic asymmetric synthesis of α-amino esters via free carbene insertion into N H bond

Zhou, Ying; Zhang, Yan; Yu, Canghai; Yue, Xin; Jiang, Feng; Guo, Wengang

doi:10.1016/j.tetlet.2023.154496

Cited by 4 publications

(3 citation statements)

References 51 publications

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“…Moreover, challenging substrates, such as benzylamine ( 26.8 ) and ammonia ( 26.9 ), also participated in the reaction, albeit with lower enantioselectivities. Soon after, Guo’s group reported a similar N–H insertion approach for the asymmetric synthesis of α-amino esters, enabled by an enantioselective proton transfer process using a chiral phosphoric acid catalyst …”

Section: Diazo Compounds As Singlet Carbene Precursorsmentioning

confidence: 99%

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

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In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement of existing reactions, as well as to the discovery of unprecedented transformations. Thus, photochemical or photocatalytic generation of both carbenes and radicals provide milder tools toward these key intermediates for many valuable transformations. However, the vast majority of the transformations represent new reactivity modes of diazo compounds, which are achieved by the photochemical decomposition of diazo compounds and photoredox catalysis. In particular, the use of a redox-active photocatalysts opens the avenue to a plethora of radical reactions. The application of these methods to diazo compounds led to discovery of transformations inaccessible by the classical reactivity associated with carbenes and metal carbenes. In most cases, diazo compounds act as radical sources but can also serve as radical acceptors. Importantly, the described processes operate under mild, practical conditions. This Review describes this subfield of diazo compound chemistry, particularly focusing on recent advancements.

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Section: Diazo Compounds As Singlet Carbene Precursorsmentioning

confidence: 99%

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

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“…Traditionally, different classes of diazo precursors are considered depending on the donor or acceptor nature of the substituents surrounding the central functional group . Donor–acceptor diazo reagents are used predominantly in N–H insertions, with much success including for asymmetric variants . However, if it becomes necessary to use acceptor–acceptor diazo reactants, one can rely on a few reported studies.…”

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confidence: 99%

General Ir-Catalyzed N–H Insertions of Diazomalonates into Aliphatic and Aromatic Amines

Zhong,

Besnard,

Lacour

2024

Org. Lett.

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A general N−H insertion reactivity of acceptor−acceptor diazo malonate reagents is reported using [Ir(cod)Cl] 2 as catalyst. A large range of amines, primary and secondary, aliphatic and aromatic, is possible. Mild temperatures, perfect substrate/reactant stoichiometry, and good functional group compatibility render the process particularly attractive for the (late-stage) functionalization of amines.

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“…In continuation of our studies on the organocatalytic asymmetric reaction of free carbenes and the related carbenoids, 25 we are curious to see whether cyclic 1-diazonaphthalen-2(1 H )-ones 26 could be employed to in situ generate the key ketene intermediates, which could be trapped with alcohols to form the desired 1 H -indene-3-carboxylates I , under mild visible-light irradiation conditions (Scheme 1c). 27 However, currently available approaches for the photochemical reaction of diazoalkanes under metal-free conditions are mainly limited to acyclic α-aryl-α-diazoacetates and their similar ketone analogues (Fig.…”

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confidence: 99%