Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

Dittami, James P.; Nie, Xiao Yi; Nie, Huixiang; Ramanathan, H.; Breining, Scott R.; Bordner, Jon; Decosta, D. L.; Kiplinger, Jeffrey P.; Reiche, P.; Ware, R.

doi:10.1021/jo00019a020

Cited by 16 publications

(11 citation statements)

References 1 publication

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“…3‐(4‐Pentenyl)cyclohex‐2‐en‐1‐one (5) :45 1 H NMR (400 MHz, CDCl 3 ): δ =5.82 (s, 1 H, CH), 5.78–5.68 (m, 1 H, CH), 4.99–4.91 (m, 2 H, CH 2 ), 2.31–1.90 (m, 10 H), 1.59–1.51 ppm (m, 2 H, CH 2 ); 13 C NMR (100 MHz, CDCl 3 ): δ =200.0, 166.5, 138.0, 125.9, 115.5, 37.5, 37.5, 33.4, 29.9, 26.2, 22.9 ppm.…”

Section: Methodsmentioning

confidence: 99%

“…3‐[2‐(1,3‐Dioxan‐2‐yl)ethyl]cyclohex‐2‐en‐1‐one (6) : 45 1 H NMR (400 MHz, CDCl 3 ): δ =5.70 (s, 1 H, CH), 4.39 (t, J =5.0 Hz, 1 H, CH), 3.93 (dd, 1 J =10.6, 2 J =5.0 Hz 2 H, CH 2 ), 3.60 (td, 1 J =12.4, 2 J =2.3 Hz, 2 H, CH 2 ), 2.21–2.14 (m, 6 H), 1.86–1.80 (m, 2 H, CH 2 ), 1.65–1.60 (m, 2 H, CH 2 ), 1.20 ppm (dt, 1 J =13.4, 2 J =1.2 Hz, 2 H, CH 2 ); 13 C NMR (100 MHz, CDCl 3 ): δ =199.6, 165.8, 125.4, 101.0, 66.7, 37.2, 32.1, 32.0, 29.6, 25.6, 22.6 ppm.…”

Section: Methodsmentioning

confidence: 99%

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Copper‐Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers

Vuagnoux‐d'Augustin

Alexakis

2007

Chemistry A European J

168

104

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Me3Al, Et3Al, and vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2-enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3CN)4]BF4 or [CuOTf]2C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous optimization of experimental conditions. It was shown that the main important parameter was the order of the introduction of the reagents. Then, the generated enantioenriched aluminium enolates and the chiral conjugate adducts were functionalized and used for subsequent reactions.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers

Vuagnoux‐d'Augustin

Alexakis

2007

Chemistry A European J

168

104

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“…This is consistent with previous observations on the rate of [2+ +2] cycloadditions versus the arylation reaction. [21] b-Aryl substrate 58 and b-cyclopropyl substrate 59 were both unreactive under the optimized reaction conditions and were re-isolated unchanged. To probe the reaction mecha-Scheme 2.…”

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confidence: 99%

Visible Light Photocatalysis of 6π Heterocyclization

et al. 2017

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Photo-mediated 6p cyclization is avaluable method for the formation of fused heterocyclic systems.H ere we demonstrate that irradiation of cyclic 2-aryloxyketones with blue LED light in the presence of an Ir III complex leads to efficient and high yielding arylation across ap anoply of substrates by energy transfer.2 -Arylthioketones and 2-arylaminoketones also cyclizee ffectively under these conditions. Quantum calculation demonstrates that the reaction proceeds via conrotatory ring closure in the triplet excited state. Subsequent suprafacial 1,4-hydrogen shift and epimerization leads to the observed cis-fused products.

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“…[21] We therefore prepared 47 by addition of the Grignard reagent from 5-bromo-1-pentene to 3-ethyoxycyclohex-2-enone followed by aqueous acidic workup. [22] Irradiation of 47 for 1 h resulted in the complete consumption of the starting material.…”

Section: Resultsmentioning

confidence: 99%

Formation of Bicyclic Pyrroles and Furans Through an Enone Allene Photocycloaddition and Fragmentation Sequence

Lutteke¹,

AlHussainy²,

Wrigstedt³

et al. 2008

Eur J Org Chem

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The [2+2] photocycloaddition of allenes 15-18, 23 and 26 was studied. Irradiation of a solution of these substrates in acetonitrile at 300 nm resulted in the clean conversion of the starting materials into a mixture of photoproducts. The major product in all cases was a bicyclic pyrrole or furan fused to an eight membered ring (43-70 % yield). The formation of these products is thought to be a result of a heteroatom-induced fragmentation of the straight adduct (7). This is supported by irradiation of the carbon analogue 32 which al-

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Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

Cited by 16 publications

References 1 publication

Copper‐Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers

Copper‐Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers

Visible Light Photocatalysis of 6π Heterocyclization

Formation of Bicyclic Pyrroles and Furans Through an Enone Allene Photocycloaddition and Fragmentation Sequence

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