Propargyloxy ketone enol ether-claisen rearrangement. Synthesis of allenyl ketones from propargyl alcohols

Reuter, J.; Salomon, Robert G.

doi:10.1016/s0040-4039(01)85593-3

Cited by 9 publications

(34 citation statements)

References 11 publications

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“…Copies of the 1 H NMR, 19 F NMR and 13 C NMR spectra can be found in the Supporting Information. were added in rapid succession.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl3) δ 7.42 (d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 5.36 (s, 1H), 4.81 (dd, J = 6.2, 2.9 Hz, 2H), 2.04 -1.81 (m, 1H), 1.66 -1.47 (m, 1H), 1.32 -1.15 (m, 16H), 1.14 -0.98 (m, 21H), 0.88 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl3) δ 206. 15, 143.29, 131.06, 127.76, 120.71, 107.62, 76.92, 75.93, 32.00, 29.51, 29.47, 29.39, 27.39, 24.84, 22.81, 18.14, 18.07, 14.26, 12.36 HRMS (ESI): m/z [M + H] + calcd for C29H50OBrSi: 521.2809; found: 521.2806.…”

Section: ((1-(4-bromophenyl)-2-vinylidenedodecyl)oxy)triisopropylsila...mentioning

confidence: 99%

“…. 13 C NMR (101 MHz, CDCl3) δ 206. 39, 143.32, 131.01, 127.82, 120.70, 105.83, 76.53, 76.06, 35.78, 33.61, 33.48, 33.16, 26.71, 26.39, 26.37, 18.14, 18.09, 12.35.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl3) δ 7.62 (d, J = 9.0 Hz, 1H), 7.44 -7.40 (d, J = 8.5 Hz, 2H), 7.34 (d, J = 9.0 Hz, 1H), 7.27 (d, J = 8.5 Hz, 2H), 6.80 -6.71 (m, 2H), 6.23 (d, J = 9.5 Hz, 1H), 5.39 (s, 1H), 4.85 (dd, J = 6.1, 2.9 Hz, 2H), 3.89 (t, J = 6.5 Hz, 2H), 2.08 -1.99 (m, 1H), 1.75 -1.64 (m, 3H), 1.54 -1.40 (m, 2H), 1.16 -0.98 (m, 22H). 13 C NMR (126 MHz, CDCl3) δ 206. 02, 162.52, 161.38, 156.10, 143.53, 143.12, 131.17, 128.79, 127.71, 120.87, 113.11, 113.09, 112.54, 107.11, 101.53, 75.91, 68.47, 28.64, 24.44, 23.79, 18.13, 18.07, 12.38.…”

Section: -((5-((4-bromophenyl)((triisopropylsilyl)oxy)methyl)hepta-56...mentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl3) δ 7.44 (d,J = 8.4 Hz,2H),4H),2H),5.44 (s,1H),2H),3.87 (dtd,J = 23.6,8.9,6.2 Hz,1H),1H), 2.16 -2.05 (m, 1H), 1.18 -0.99 (m, 21H). 13 C NMR (126 MHz,CDCl3) δ 205.95,158.09,142.68,132.28,131.30,127.70,121.09,116.41,112.79,103.60,77.55,75.81,66.60,25.00,18.14,18.07,12.37.…”

Section: Hrms (Esimentioning

confidence: 99%

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Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers through Iron-Catalyzed Regioselective C(sp2)–H Functionalization of Allenes

Ding

Wang

2022

Synthesis

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We report a synthesis of allenylic silyl ethers through iron-catalyzed functionalization of the C(sp2)−H bonds of monosubstituted alkylallenes. In the presence of a cyclopentadienyliron dicarbonyl based catalyst and triisopropylsilyl triflate as a silylation agent, a variety of aryl aldehydes were suitable coupling partners in this transformation, furnishing a collection of 1,1-disubstituted allenylic triisopropylsilyl ethers as products in moderate to excellent yields as a single regioisomer. Lithium bistriflimide was identified as a critical additive in this transformation. The optimized protocol was scalable, and the products were amenable to further transformation to give a number of unsaturated, polyfunctional derivatives.

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“…Copies of the 1 H NMR, 19 F NMR and 13 C NMR spectra can be found in the Supporting Information. were added in rapid succession.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Section: ((1-(4-bromophenyl)-2-vinylidenedodecyl)oxy)triisopropylsila...mentioning

confidence: 99%

“…. 13 C NMR (101 MHz, CDCl3) δ 206. 39, 143.32, 131.01, 127.82, 120.70, 105.83, 76.53, 76.06, 35.78, 33.61, 33.48, 33.16, 26.71, 26.39, 26.37, 18.14, 18.09, 12.35.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Section: -((5-((4-bromophenyl)((triisopropylsilyl)oxy)methyl)hepta-56...mentioning

confidence: 99%

Section: Hrms (Esimentioning

confidence: 99%

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