Advances in the cobalt-catalysed Pauson-Khand reaction: Development of a sulfide-promoted, microwave-assisted protocol
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DOI: 10.1016/j.tet.2020.131805
Abstract: Abstract The development of a sulfide-promoted, microwave-assisted Pauson-Khand reaction has enabled the formation of fused cyclopentenones using sub-stoichiometric quantities of a cobalt mediator over rapid reaction times and with no requirement for an external source… read more here.
Keywords: khand reaction; development sulfide; reaction; pauson khand ... See more keywords
Type-II Pauson-Khand reaction of 1,8-enyne in the attempt of building 7/5 ring of (-)-caribenol A and DFT understanding
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DOI: 10.1016/j.tetlet.2019.151001
Abstract: Abstract An attempt to access the fused 7/5 ring of the highly biologically active terpenoid caribenol A by employing intramolecular Pauson-Khand reaction of 1,8-enyne gave bridged 8-5 ring, the type-II Pauson-Khand reaction product. DFT study… read more here.
Keywords: reaction enyne; khand reaction; pauson khand;
Carbamate as an accelerating group in intermolecular Pauson-Khand reaction
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DOI: 10.1016/j.tetlet.2020.151974
Abstract: Abstract The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the… read more here.
Keywords: khand reaction; reaction; pauson khand; carbamate ... See more keywords
Computational Study on the Co-Mediated Intramolecular Pauson–Khand Reaction of Fluorinated and Chiral N-Tethered 1,7-Enynes
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DOI: 10.1021/acs.organomet.2c00227
Abstract: The Co2(CO)8-mediated intramolecular Pauson–Khand reaction is an elegant approach to obtain cyclopentenone derivatives containing asymmetric centers. In this work, we employed density functional theory calculations at the M11/6-311+G(d,p) level of theory to investigate the mechanism… read more here.
Keywords: mediated intramolecular; pauson khand; intramolecular pauson; khand reaction ... See more keywords
Rh(I)-Catalyzed Allenic Pauson-Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.1c03951
Abstract: Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson-Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the… read more here.
Keywords: allenic pauson; pauson khand; khand reaction; thapsigargin ... See more keywords
Oxygenated Cyclopentenones via the Pauson–Khand Reaction of Silyl Enol Ether Substrates
Sign Up to like & getrecommendations! Published in 2022 at "Organic Letters"
DOI: 10.1021/acs.orglett.2c00856
Abstract: We report here the application of silyl enol ether moieties as efficient alkene coupling partners within cobalt-mediated intramolecular Pauson–Khand reactions. This cyclization strategy delivers synthetically valuable oxygenated cyclopentenone products in yields of ≤93% from both… read more here.
Keywords: enol ether; pauson khand; oxygenated cyclopentenones; silyl enol ... See more keywords
Vinyl Fluorides: Competent Olefinic Counterparts in the Intramolecular Pauson-Khand Reaction.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b00509
Abstract: Despite the great advances achieved in the Pauson-Khand reaction and the ever-increasing demand for fluorinated compounds, the use of vinyl fluorides as olefinic counterparts in the above-mentioned transformation had been completely overlooked. Herein, we describe,… read more here.
Keywords: vinyl fluorides; khand reaction; olefinic counterparts; pauson khand ... See more keywords
The Fluoro-Pauson-Khand Reaction in the Synthesis of Enantioenriched Nitrogenated Bicycles Bearing a Quaternary C-F Stereogenic Center.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b02557
Abstract: A variety of enantioenriched fluorinated 6H-cyclopenta[c]pyridin-6-one bicycles, a scaffold present in several classes of monoterpenic alkaloids with varied biological activity, were synthesized in just five steps from simple aldehyde starting materials. The synthesis presented wide… read more here.
Keywords: reaction synthesis; synthesis enantioenriched; fluoro pauson; pauson khand ... See more keywords
Reductive Aza-Pauson-Khand Reaction of Nitriles.
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DOI: 10.1021/jacs.3c01656
Abstract: γ-Lactams are valuable heterocycles in synthetic chemistry and drug development. Here, we report a reductive aza-Pauson-Khand reaction (aza-PKR) of an alkyne, a nitrile, and Co2(CO)8. A wide array of bicyclic α,β-unsaturated γ-lactams containing two adjacent… read more here.
Keywords: reductive aza; pauson khand; reaction; khand reaction ... See more keywords
Study of the Pauson–Khand reaction in flow over alkynylphenyl vinyl ethers: towards the synthesis of tricyclic multisubstituted benzofurans
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DOI: 10.1039/d2ra01062c
Abstract: The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson–Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the… read more here.
Keywords: pauson khand; vinyl ethers; reaction; khand reaction ... See more keywords
Tungsten-Promoted Hetero-Pauson–Khand Cycloaddition: Application to the Total Synthesis of (–)-Allosecurinine
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DOI: 10.1055/s-0037-1612063
Abstract: Herein, we report a concise enantioselective synthesis of (–)-allosecurinine, a tetracyclic Securinega alkaloid featuring an α,β-unsaturated γ-lactone moiety. Starting from inexpensive and readily available trans-l-hydroxyproline, our strategy entails a rare late-stage [2+2+1]-hetero-Pauson–Khand cycloaddition between a… read more here.
Keywords: allosecurinine; hetero pauson; synthesis; pauson khand ... See more keywords