Stereoselectivity of intramolecular dicobalt octacarbonyl alkene-alkyne cyclizations: short synthesis of dl-coriolin

Exon, Christopher; Magnus, Philip

doi:10.1021/ja00346a063

Cited by 135 publications

(29 citation statements)

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“…S11 †). In particular, the (10,2) and (8,4) are shifted from 1055 nm to 1062 nm and from 1113 nm to 1118 nm, respectively. Nevertheless, shift of only 0-1 nm is observed for (9,4) and (7,6) peaks.…”

Section: Experimental Investigationsmentioning

confidence: 98%

“…[1][2][3] This chemical transformation, usually termed as the Pauson-Khand reaction (PKR), has gained attention within the field of organic chemistry since many natural products can be synthesized from it. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Besides cobalt, also other transition metals perform well in the PKR such as rhodium, [19][20][21] ruthenium, 22,23 palladium, 24 iridium, 25,26 iron, 27,28 tungsten, 29 molybdenum, 30,31 and chromium. 32,33 The PKR depends upon steric and electronic factors.…”

Section: Introductionmentioning

confidence: 99%

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Regioselectivity of the Pauson–Khand reaction in single-walled carbon nanotubes

et al. 2018

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Chemical functionalization of nanotubes, in which their properties can be combined with those of other classes of materials, is fundamental to improve the physicochemical properties of nanotubes for potential technological applications. In this work, we theoretically and experimentally examine the Pauson-Khand reaction (PKR) on zig-zag, armchair, and chiral single-walled carbon nanotubes (SWCNTs). Our benchmarked density functional theory (DFT) calculations show that an alternative pathway to the widely accepted Magnus reaction pathway has significantly lower energy barriers, thus suggesting the use of this alternative pathway to predict whether a PKR on SWCNTs is favored or hampered. Accessible energy barriers of up to 16 kcal mol-1 are estimated and our results suggest that semiconducting SWCNTs react faster than metallic ones, although both types can be functionalized. Guided by our theoretical predictions, cyclopentenones are successfully attached to SWCNTs by heating and are, subsequently, characterized in the laboratory.

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Section: Experimental Investigationsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Regioselectivity of the Pauson–Khand reaction in single-walled carbon nanotubes

et al. 2018

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“…The intramolecular version of the reaction has gained much popularity, because it can afford complex cyclopentenone-fused ring systems. [47][48][49][50][51][52] Herein, we report the synthesis of novel isoquinoline-substituted 1,2,3-triazole derivatives through one-pot synthesis method and also isoquinoline-substituted dihydropyran and cyclopentenone pyran derivatives by ring closing metathesis and…”

Section: Figure 1 Important Isoquinoline Derivativesmentioning

confidence: 99%

<strong>Isoquinoline-substituted hybrid compounds: synthesis and computational studies</strong>

Gümüş

Yenidede

2016

Proceedings of the 20th International Electronic Conference on Synthetic Organic Chemistry

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The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazoles from isoquinoline-substituted homopropargyl alcohol backbone is described (42-88% yields). A ring closing metathesis (RCM) reaction and an intramolecular Pauson-Khand reaction (PKR) of enyne system derived from a homopropargyl alcohol backbone to afford the corresponding isoquinoline-substituted dihydropyran and cyclopentenone-pyran, respectively, are also described (54% and 78% yields). Information about the structural, electronic and physico-chemical properties of the novel compounds, obtained by density functional theory application, is also reported.

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“…16 Allenes can also provide the alkene component (Scheme 7.14); which of the two alkene moieties of the allene participates depends upon the precise structure. The reaction is more efficient, and issues of regioselectivity are solved, when the reaction is carried out in an intramolecular fashion (Scheme 7.13).…”

Section: The Pauson-khand Reactionmentioning

confidence: 99%