Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

Urabe, Fumiya; Miyamoto, Shohei; Takahashi, Keisuke; Ishihara, Jun; Hatakeyama, Susumi

doi:10.1021/ol403746r

Cited by 44 publications

(20 citation statements)

References 74 publications

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“…22 In this respect, further investigations of catalytic reactions of diazocarbonyl compounds of different types with α,β-unsaturated δ-N-substituted amino esters are undeniably of great importance and interest. 22 In this respect, further investigations of catalytic reactions of diazocarbonyl compounds of different types with α,β-unsaturated δ-N-substituted amino esters are undeniably of great importance and interest.…”

Section: Discussionmentioning

confidence: 99%

Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

et al. 2015

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Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate.

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Section: Discussionmentioning

confidence: 99%

Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

et al. 2015

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“…1 H-NMR and 13 C-NMR spectra were recorded on a 400 MHz Bruker spectrometer. Low resolution mass spectra were obtained on a Agilent Technologies 7820A GC coupled to a mass spectrometer 5977E unit using electron impact at 70 eV.…”

Section: Methodsmentioning

confidence: 99%

“…Homopropargyl alcohols are very useful synthetic intermediates in organic synthesis [1] [2]. Numerous methods for their preparation have been developed, using a wide variety of organometallic reagents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Aromatic Homopropargyl Alcohols

Umaña¹,

Arias²,

Cabezas³

2017

IJOC

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Several aromatic homopropargyl alcohols, and derivatives were prepared by one-pot reaction of 1,3-dilithiopropyne (or its equivalent) with aldehydes and ketones. The antibacterial activity, of alcohols thus prepared, against Gram (+) and Gram (−) bacteria was tested. This activity varies depending upon substitution on the homopropargyl alcohol unit. Apparently, the benzene ring and the free hydroxyl group (or its alcoxide) are needed, in the homopropargyl alcohol unit, to be biologically active.

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“…Recently, a more direct method was developed by Urabe et al (Scheme 53). 190 In this case the ether formation is directly followed by a Lewis acid-catalyzed cyclization, yielding 2-methylene THF in very good yield, but moderate diastereoselectivity. The group of Mascarenas/Lopez also described a cascade cycloaddition leading to various sizes of oxa-bridged carbocycles, among which some THF were synthesized.…”

Section: Scheme 52: Enantioselective Thf Synthesis By One-pot Allylbomentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

Cited by 44 publications

References 74 publications

Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii)–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines

Synthesis and Antibacterial Activity of Aromatic Homopropargyl Alcohols

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

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