α-Haloenamides: Synthesis and Subsequent Transformations

Feray, Laurence; Bertrand, M.; galibert, aurelien

doi:10.1055/a-1921-8710

Cited by 3 publications

(1 citation statement)

References 63 publications

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“…Therefore, tremendous efforts have been devoted to the synthesis of such important frameworks over the past decades. 54 The hydrohalogenation of ynamides, featuring high atom- and step-economy, is arguably the simplest and most straightforward strategy. On the basis of the addition mode to deliver regio- and stereoisomers, the adducts can be classified into three types: the syn -α-adduct, anti -α-adduct and anti -β-adduct, while the syn -β-adduct has not been reported yet.…”

Section: C–x Bond Formationmentioning

confidence: 99%

Catalytic intermolecular hydrofunctionalizations of ynamides

Zhao,

Jia,

2024

Org. Chem. Front.

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Section: C–x Bond Formationmentioning

confidence: 99%

Catalytic intermolecular hydrofunctionalizations of ynamides

Zhao,

Jia,

2024

Org. Chem. Front.

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Synthesis of Enamides through Hydro‐Functionalization of Ynamides

Mishra,

Sekhar Pati,

Das

2024

Eur J Org Chem

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Most of the methods for the synthesis of functionalized enamides from ynamides were developed in the last two decades showing the contemporary interest in the exploration of ynamide chemistry. The utilization of the intrinsic reactivity of the ynamide triple bond through keteniminium intermediacy, coordination with metals, and as a radical acceptor toward the development of strategies for the synthesis of functionalized enamides reflect the constant strive and creativity in the design and execution of synthetic methods. The present review summarizes the synthetic strategies developed during the last two decades and is divided into the sections depending on the type of hydrofunctionalization reaction. It may be predicted that this field of chemistry will continue to grow exponentially in the coming years and the ready availability of a wide range of ynamides now provides an excellent opportunity to further enrich mainstream synthetic methodologies.

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HFIP-Mediated, Highly Chemo-, Regio-, and Stereoselective Hydrofunctionalizations of Ynamides: Access to Stereodefined Alkenes Bearing Drugs and Natural Products

Satyanarayana,

Chatterjee

2024

J. Org. Chem.

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We disclose a sustainable and versatile synthetic strategy for the highly chemo-, regio-, and stereoselective hydrofunctionalizations of ynamides, through its activation by a solvent, HFIP, to access a wide variety of stereodefined ketene N,N, N,O, N,S, and N,Se acetals in high yield at room temperature. The reaction proceeded through the formation of the reactive keteniminium ion intermediate, formed via protonation at the β-carbon of ynamide by HFIP, followed by an attack of a nucleophile (syn-addition) at the α-carbon. When ynamides are treated with only HFIP at room temperature, the HFIP addition products of ynamides are formed in a 100% atom-economic fashion; however, in the presence of a stronger N-/O-/S-/Se-based nucleophile, the corresponding syn-hydroheterofunctionalized products are formed. Notably, HFIP played multiple roles, such as a reagent, in particular, a Brønsted acid, nucleophile, as well as solvent. Interestingly, HFIP is found to be unique for this transformation. Notably, this strategy is utilized for the late-stage functionalization of several marketed drugs and natural products, and it also enables the connection of two different drugs or a drug and a natural product through chemical bonds. Significantly, HFIP was recovered after the reaction and reused for consecutive reactions.

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α-Haloenamides: Synthesis and Subsequent Transformations

Cited by 3 publications

References 63 publications

Catalytic intermolecular hydrofunctionalizations of ynamides

Catalytic intermolecular hydrofunctionalizations of ynamides

Synthesis of Enamides through Hydro‐Functionalization of Ynamides

HFIP-Mediated, Highly Chemo-, Regio-, and Stereoselective Hydrofunctionalizations of Ynamides: Access to Stereodefined Alkenes Bearing Drugs and Natural Products

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