Excellent Preparation of Azetidin-3-Ones from Propargylic Alcohols by Gold-Catalysis

Tan, Peng; Xiang, Jian Nan

doi:10.4028/www.scientific.net/amr.634-638.970

Cited by 2 publications

(3 citation statements)

References 24 publications

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“…It was later shown that several other sulfonyl-protecting groups were tolerated in this reaction. 784 Notably, the tert -butanesulfinamide group allowed preparation of enantioenriched products by employing the chemistry of Ellman. 785 …”

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

“…It was later shown that several other sulfonylprotecting groups were tolerated in this reaction. 784 Notably, the tert-butanesulfinamide group allowed preparation of enantioenriched products by employing the chemistry of Ellman. 785 Although the formation of oxetan-3-ones and thietane-3-ones under oxidative gold catalysis has been sporadically re-ported, 786,787 the only gold-catalyzed preparative methods for the synthesis of heteroatom-containing 4-membered rings remain the two protocols developed by the group of Zhang.…”

Section: Synthesis Of Heteroatom-containing 4-membered Ringsmentioning

confidence: 99%

“…By carefully tuning the reaction conditions, azetidin-3-ones with different substitution patterns and protecting groups could be obtained. It was later shown that several other sulfonyl-protecting groups were tolerated in this reaction . Notably, the tert -butanesulfinamide group allowed preparation of enantioenriched products by employing the chemistry of Ellman …”

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

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Gold-Catalyzed Synthesis of Small Rings

et al. 2020

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Three- and four-membered rings, widespread motifs in nature and medicinal chemistry, have fascinated chemists ever since their discovery. However, due to energetic considerations, small rings are often difficult to assemble. In this regard, homogeneous gold catalysis has emerged as a powerful tool to construct these highly strained carbocycles. This review aims to provide a comprehensive summary of all the major advances and discoveries made in the gold-catalyzed synthesis of cyclopropanes, cyclopropenes, cyclobutanes, cyclobutenes, and their corresponding heterocyclic or heterosubstituted analogs.

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Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

Section: Synthesis Of Heteroatom-containing 4-membered Ringsmentioning

confidence: 99%

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

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Gold-Catalyzed Synthesis of Small Rings

et al. 2020

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Gold-catalyzed synthesis of small-sized carbo- and heterocyclic compounds: A review

Kadiyala,

Goutham,

Yamini

et al. 2024

Heterocyclic Communications

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Research on gold catalysis has flourished over the last 20 years, and gold catalysts are now acknowledged as the “best choice” for a range of organic transformations. Gold complexes have emerged as promising candidates for this use in recent years because of their high reactivity, which enables them to induce a broad range of transformations under mild conditions. Extensive demonstrations have showcased the extraordinary efficiency of synthesizing complex organic compounds from the basic starting components. In addition to its traditional applications in catalysis, gold catalysis has expanded to include the total synthesis of natural compounds, which is a complex and demanding undertaking. The class of molecules known as carbo- and heterocycles, which is arguably the most important, has a significant impact on the synthesis of agrochemicals and pharmaceuticals among the numerous additional products made possible by the novel procedures pioneered. The main topic of this review is how to use Au salts in homogeneous catalysis to create cyclization processes for small heterocyclic and carbocyclic systems. This study gives an overview of most of the books and articles written after 2013 that discuss making three- and four-membered carbo- and heterocyclic rings with gold as a catalyst. We have made every effort to include all outstanding reports on this subject; nonetheless, we apologize for any omissions.

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Excellent Preparation of Azetidin-3-Ones from Propargylic Alcohols by Gold-Catalysis

Abstract: Azetidin-3-ones are important heterocycles in organic synthesis and pharmaceutical chemistry. With gold-catalyzed alkyne intermolecular oxidation, these versatile heterocycles can be prepared in three steps from readily available propargylic alcohols with high efficiencies.

Cited by 2 publications

References 24 publications

Gold-Catalyzed Synthesis of Small Rings

Gold-Catalyzed Synthesis of Small Rings

Gold-catalyzed synthesis of small-sized carbo- and heterocyclic compounds: A review

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