A new approach to 2,2-disubstituted chromenes and tetrahydroquinolines through intramolecular cyclization of chiral 3,4-epoxy alcohols

Goujon, Jean-Yves; Zammattio, Françoise; Chrétien, Jacques R.; Beaudet, Isabelle

doi:10.1016/j.tet.2004.03.010

Cited by 32 publications

(19 citation statements)

References 52 publications

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“…Various methods have been developed to attain the benzopyran core,7 such as: Wittig olefinations,8 oxidation of the corresponding chromanes,9 Pd‐catalyzed oxidative cyclization of O ‐allylphenols,10 ring‐closing metathesis,11 oxa‐Michael/aldol sequence,12 epoxide ring‐opening,13 direct functionalization of simple chromenes or chromene acetals,14 O ‐quinone methide cyclization under thermal conditions,15 Morita–Baylis–Hillman reaction,16 Petasis reaction,17 cobalt‐catalyzed carbene radicals insertion,18 propargyl ether hydroarylation 19. In addition, Pd‐catalyzed asymmetric allylic substitution was developed to generate optically active chromanes that were subsequently oxidized to the corresponding chromenes 20.…”

Section: Methodsmentioning

confidence: 99%

2H‐Chromenes Generated by an Iron(III) Complex‐Catalyzed Allylic Cyclization

2015

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Section: Methodsmentioning

confidence: 99%

2H‐Chromenes Generated by an Iron(III) Complex‐Catalyzed Allylic Cyclization

2015

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“…3‐Methyl‐1‐(2‐tosylaminophenyl)‐but‐3‐en‐1‐ol 13 b :58 Compound 13 b was obtained from 2‐tosylamino‐benzaldehyde (1.0 mmol) and polymer 1 b as a white solid (295 mg, 89 %) after purification by flash chromatography (petroleum ether/ethyl acetate 8:2, R f = 0.45); 1 H NMR: δ = 1.69 (s, 3 H), 2.19 (dd, J = 4.2, 13.8 Hz, 1 H), 2.28 (dd, J = 9.9, 13.8 Hz, 1 H), 2.37 (s, 3 H), 2.56 (br s, 1 H), 4.68 (dd, J = 9.9, 4.2 Hz, 1 H), 4.75 (s, 1 H), 4.92 (s, 1 H), 7.04 (m, 2 H), 7.18–7.24 (m, 3 H), 7.49 (d, J = 8.1 Hz, 1 H), 7.70 (d, J = 8.1 Hz, 2 H), 8.57 (s, 1 H) ppm; 13 C NMR: δ = 21.4, 22.0, 45.1, 71.3, 114.6, 121.7, 124.4, 127.0, 127.5, 128.4, 129.5, 132.0, 135.8, 136.9, 141.3, 143.6 ppm; MS (EI 70 eV): m/z (relative intensity): 331 (4), 275 (5), 158 (100), 143 (30), 120 (41), 91 (36), 65 (18) ppm; IR (KBr): $\tilde \nu $ = 3491, 3239, 2922, 1159 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Preparation of Allyltin Reagents Grafted on Solid Support: Clean and Easily Recyclable Reagents for Allylation of Aldehydes

Chrétien

Zammattio

Gauthier

et al. 2006

Chemistry A European J

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The preparation of polymer-supported allyltin reagents was shown to be possible for both unfunctionalized and functionalized allyl units. These reagents were treated with aldehydes in the presence of cerium(III) or indium(III) salts to afford high yields of homoallylic alcohols, practically uncontaminated with organotin residues (less than 5 ppm). Some mechanism aspects are briefly discussed and the potential for regeneration and reuse of these supported reagents is pointed out.

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“…As shown in Scheme , the synthesis involves the reaction between N ‐benzylindole ( 85 ) and 2‐(tosylamino)benzaldehyde ( 87 ) 61…”

Section: Total Syntheses Of Neocryptolepinementioning

confidence: 99%

Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

Cong

Liu

Ferré

et al. 2014

Chemistry A European J

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Bacterial bioluminescence (BL) has been successfully applied in water-quality monitoring and in vivo imaging. The attention of researchers has been attracted for several decades, but the mechanism of bacterial BL is still largely unknown due to the complexity of the multistep reaction process. Debates mainly focus on three key questions: How is the bioluminophore produced? What is the exact chemical form of the bioluminophore? How does the protein environment affect the light emission? Using quantum mechanics (QM), combined QM and molecular mechanics (QM/MM) and molecular dynamic (MD) calculations in gas-phase, solvent and protein environments, the entire process of bacterial BL was investigated, from flavin reduction to light emission. This investigation revealed that: 1) the chemiluminescent decomposition of flavin peroxyhemiacetal does not occur through the intramolecular chemical initiated electron exchange luminescence (CIEEL) or the "dioxirane" mechanism, as suggested in the literature. Instead, the decomposition occurs according to the charge-transfer initiated luminescence (CTIL) mechanism for the thermolysis of dioxetanone. 2) The first excited state of 4a-hydroxy-4a,5-dihydroFMN (HFOH) was affirmed to be the bioluminophore of bacterial BL. This study provides details regarding the mechanism by which bacterial BL is produced and is helpful in understanding bacterial BL in general.

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A new approach to 2,2-disubstituted chromenes and tetrahydroquinolines through intramolecular cyclization of chiral 3,4-epoxy alcohols

Cited by 32 publications

References 52 publications

2H‐Chromenes Generated by an Iron(III) Complex‐Catalyzed Allylic Cyclization

2H‐Chromenes Generated by an Iron(III) Complex‐Catalyzed Allylic Cyclization

Preparation of Allyltin Reagents Grafted on Solid Support: Clean and Easily Recyclable Reagents for Allylation of Aldehydes

Understanding Bacterial Bioluminescence: A Theoretical Study of the Entire Process, from Reduced Flavin to Light Emission

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