Synthesis of Allenamides and Structurally Related Compounds by a Gold‐Catalyzed Hydride Shift Process

Zhao, Qun; Gagosz, Fabien

doi:10.1002/adsc.201700615

Cited by 24 publications

(18 citation statements)

References 75 publications

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“…Further synthetic elaboration of this regioselective process is highlighted by preparing cyclic silyl ethers and bicylclic ketones in a separate work [283] . While mentioning on hydride migration, Zhao and Gagosz disclosed the rearrangement of ynamides possessing −OBn group at the propargylic site into allenamides via Au(I)‐catalyzed regioselective 1,5‐hydride shift [284] . Wang et al .…”

Section: Miscellaneous Rearrangementsmentioning

confidence: 99%

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Praveen

2020

Asian J Org Chem

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Homogeneous gold catalysis for connection and disconnection of carbon-carbon (CÀ C) as well as carbonheteroatom (CÀ X) bond constitutes an important zone in molecular chemistry, since all new or existing organic synthesis relies on the transformation of these chemical bonds. Among the diaspora of molecular transformations, rearrangement and shift reactions occupy a special place in organic chemistry, as they enable the synthesis of molecules of increased complexity from simple precursors. However, the rearrangement in substrates possessing more than one potential reaction site produce more than one isomer and could result in regioselective issues. This challenge of selective synthesis of one regisomer over the other was fairly addressed by gold catalysis on various occasions. To this end, the prowess of homogeneous gold catalysis towards regioselective molecular rearrangement reactions and the contributing parameters are comprehensively reviewed. Also, synthetic applicability of regioselective rearrangements by gold catalysis in total and formal synthesis of several natural products was emphasized.This review also covers the emergence of gold catalyzed migratory/shift selective reactions and could be beneficial for synthetic and medicinal chemists.

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Section: Miscellaneous Rearrangementsmentioning

confidence: 99%

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Praveen

2020

Asian J Org Chem

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“…In 2017, Zhao et al reported the synthesis of N -allenamides and pyrroles ( Scheme 4 ) [ 40 ]. Under gold 42 catalysis, N -alkynylpyrrole bearing a benzyloxy group at the propargylic position 40 was converted into the corresponding allenepyrrole 41 , expelling benzaldehyde 43 .…”

Section: Synthesis Of [12]-fused Polyheterocyclic Structuresmentioning

confidence: 99%

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Horsten¹,

Dehaen²

2021

Molecules

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This review focuses on the synthesis of polyheterocyclic structures with a variety of medicinal and optoelectronic applications, starting from readily available 4,5,6,7-tetrahydroindol-4-one analogs. First, routes toward the 4,5,6,7-tetrahydroindol-4-one starting materials are summarized, followed by synthetic pathways towards polyheterocyclic structures which are categorized based on the size and attachment point of the newly formed (hetero)cyclic ring.

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“…In 2012, Rabasso published a [2,3]-sigmatropic rearrangement of N -alkynyl amides [118]. The following year, 2013, during their investigations into the selective reduction of amino-allenephosphonates, Rabasso expanded the scope of their [2,3]-sigmatropic rearrangement to include N -alkynyl indole (Scheme 75) [119]. The researchers found that compound 279 , underwent a [2,3]-rearrangement when treated with diethyl chlorophosphite, giving N -allenylphosphate 281 in a 78% yield.…”

Section: Reactions Of N-alkynyl Azolesmentioning

confidence: 99%

Preparation and Utility of N-Alkynyl Azoles in Synthesis

Reinus

Kerwin

2019

Molecules

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Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis.

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Synthesis of Allenamides and Structurally Related Compounds by a Gold‐Catalyzed Hydride Shift Process

Cited by 24 publications

References 75 publications

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Preparation and Utility of N-Alkynyl Azoles in Synthesis

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