On the Way to an Oxidative
Hosomi-Sakurai Reaction

Cyrille Sabot; Bruno Commare; Marc-Alexandre Duceppe; Salima Nahi; Kimiaka C. Guérard; Sylvain Canesi

doi:10.1055/s-0028-1087369

LETTER

On the Way to an Oxidative Hosomi-Sakurai Reaction

Cyrille Sabot, Bruno Commare, Marc-Alexandre Duceppe, Salima Nahi, Kimiaka C. Guérard, Sylvain Canesi*
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada
Fax: +1(514)9874054; e-Mail: canesi.sylvain@uqam.ca;

Abstract

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Abstract

An oxidative allylation process mediated by a hypervalent iodine reagent has been performed on polysubstituted phenols. This reaction, occurring in useful to good yields, leads to a rapid access to dienones containing a quaternary carbon center.

Key words

hypervalent iodine - allyltrimethylsilane - substitued phenols - oxidative allylation

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References

References and Notes

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Analytical Data
IR: ca. 1645 (CO) cm^-¹.
Compound 13b: ^¹H NMR (300 MHz, CDCl₃): δ = 6.33 (s,
2 H), 5.43 (m, 1 H), 4.92 (m, 2 H), 2.23 (d, 2 H, J = 7.8 Hz), 1.53 (m, 2 H), 1.19 (m, 22 H), 0.99 (m, 2 H), 0.80 (t, 3 H,
J = 6.6 Hz). ^¹³C NMR (150 MHz, CDCl₃): δ = 187.3, 148.2, 145.7, 133.5, 118.1, 45.3, 44.1, 40.1, 35.1, 32.4, 29.9, 24.3, 22.7, 14.2. ESI-HRMS: m/z calcd for C₂₂H₃₆ONa [M + Na]⁺: 339.2658; found: 339.2662.
Compound 13c: ^¹H NMR (300 MHz, CDCl₃): δ = 6.39 (s,
2 H), 5.43 (m, 1 H), 4.93 (m, 2 H), 2.32 (d, 2 H, J = 7.5 Hz), 1.83 (h, 1 H, J = 6.6 Hz), 1.21 (s, 18 H), 0.84 (d, 6 H, J = 6.6 Hz). ^¹³C NMR (150 MHz, CDCl₃): δ = 187.4, 148.8, 144.3, 133.8, 117.8, 46.4, 42.4, 36.3, 35.3, 29.9, 18.2. ESI-HRMS: m/z calcd for C₂₀H₃₃O [M + H]⁺: 289.2525; found: 289.2529.
Compound 13d: ^¹H NMR (300 MHz, CDCl₃): δ = 6.44 (s, 2 H), 5.48 (m, 1 H), 4.97 (m, 2 H), 3.42 (t, 2 H, J = 7.2 Hz), 2.30 (d, 2 H, J = 7.8 Hz), 1.92 (t, 2 H, J = 7.2 Hz), 1.27 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.9, 148.4, 145.0, 132.7, 118.8, 60.0, 45.4, 42.9, 42.8, 35.2, 29.8 ESI-HRMS: m/z calcd for C₁₉H₃₀O₂Na [M + Na]⁺: 313.2138; found: 313.2138.
Compound 13e: ^¹H NMR (300 MHz, CDCl₃): δ = 6.50 (s,
2 H), 5.49 (m, 1 H), 4.97 (m, 2 H), 3.48 (s, 2 H), 2.35 (d,
2 H, J = 7.2 Hz), 1.22 (s, 18 H), 0.88 (s, 9 H), 0.03 (s, 6 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 187.2, 148.8, 143.0, 133.4, 118.3, 69.1, 45.7, 40.5, 35.2, 29.9, 26.1, 18.5, -5,1. ESI-HRMS: m/z calcd for C₂₄H₄₃O₂Si [M + H]⁺: 391.3026; found: 391.3008.
Compound 13f: ^¹H NMR (300 MHz, CDCl₃): δ = 7.56 (d,
2 H, J = 7.5 Hz), 7.20 (d, 2 H, J = 7.5 Hz), 6.25 (s, 2 H), 5.35 (m, 1 H), 4.87 (m, 2 H), 4.29 (m, 1 H), 2.55 (q, 2 H, J = 6.6 Hz), 2.32 (s, 3 H), 2.17 (d, 2 H, J = 7.5 Hz), 1.79 (t, 2 H, J = 6.6 Hz), 1.10 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.5, 149.1, 144.2, 144.0, 136.6, 132.3, 130.1, 127.3, 119.0, 45.3, 43.1, 40.1, 39.7, 35.2, 29.8, 21.8. ESI-HRMS: m/z calcd for C₂₆H₃₇NO₃SNa [M + Na]⁺: 466.2386; found: 466.2378.
Compound 13g: ^¹H NMR (300 MHz, CDCl₃): δ = 6.49 (s,
2 H), 5.50 (m, 1 H), 4.01 (m, 2 H), 3.54 (s, 3 H), 2.54 (s, 2 H), 2.35 (d, 2 H, J = 7.2 Hz), 1.21 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.7, 170.7, 148.1, 143.4, 132.5, 119.3, 51.7, 44.6, 44.3, 42.0, 35.2, 29.8. ESI-HRMS: m/z calcd for C₂₀H₃₁O₃ [M + H]⁺: 319.2267; found: 319.2267.

<A NAME="RS07408ST-15">15</A> Clemo GR. Haworth RD. Walton E. J. Chem. Soc. 1930, 1110

<A NAME="RS07408ST-16">16</A> Thadani AN. Huang Y. Rawal VH. Org. Lett. 2007, 9: 3873

Analytical Data Compound 17a: ^¹H NMR (300 MHz, CDCl₃): δ = 6.86 (s,
2 H), 5.52 (m, 1 H), 4.99 (m, 2 H), 2.26 (d, 2 H, J = 7.2 Hz), 1.20 (s, 3 H), 0.16 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃):
δ = 192.0, 162.4, 140.7, 133.3, 118.6, 45.2, 41.4, 25.5, -0.9. ESI-HRMS: m/z calcd for C₁₆H₂₉OSi₂ [M + H]⁺: 293.1751; found: 293.1753.
Compound 17b: ^¹H NMR (300 MHz, CDCl₃): δ = 6.77 (s,
2 H), 5.51 (m, 1 H), 4.99 (dd, 1 H, J = 8.7, 1.2 Hz), 4.96 (dd, 1 H, J = 18.0, 1.2 Hz), 2.29 (d, 2 H, J = 7.2 Hz), 1.63 (q,
2 H, J = 7.8 Hz), 0.68 (t, 3 H, J = 7.8 Hz), 0.16 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 192.4, 161.3, 143.0, 133.3, 118.3, 46.1, 44.3, 32.1, 9.3, -0.8. ESI-HRMS: m/z calcd for C₁₇H₃₁OSi₂ [M + H]⁺: 307.1908; found: 307.1909.
Compound 17c: ^¹H NMR (300 MHz, CDCl₃): δ = 7.30 (m,
5 H), 7.00 (s, 2 H), 5.56 (m, 1 H), 5.05 (m, 2 H), 2.80 (d,
2 H, J = 7.2 Hz), 0.18 (18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 192.1, 160.7, 141.1, 140.8, 132.9, 129.3, 127.6, 127.0, 119.0, 48.6, 42.3, -0.9. ESI-HRMS: m/z calcd for C₂₁H₃₁OSi₂ [M + H]⁺: 355.1908; found: 355.1914.
Compound 17d: ^¹H NMR (300 MHz, CDCl₃): δ = 6.86 (s,
2 H), 5.47 (m, 1 H), 4.98 (m, 2 H), 3.42 (t, 2 H, J = 6.9 Hz), 2.29 (d, 2 H, J = 7.2 Hz), 1.92 (t, 2 H, J = 6.9 Hz), 0.14 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 192.1, 160.9, 142.7, 132.5, 119.1, 60.0, 44.7, 44.4, 42.0, -0.9. ESI-HRMS: m/z calcd for C₁₇H₃₁O₂Si₂ [M + H]⁺: 323.1857; found: 323.1853.

Analytical Data
Compound 21a: ^¹H NMR (300 MHz, CDCl₃): δ = 6.91 (d,
1 H, J = 2.7 Hz), 6.55 (1 H, d, J = 2.7 Hz), 5.55 (m, 1 H), 5.04 (m, 2 H), 2.34 (d, 2 H, J = 8.1 Hz), 1.27 (s, 3 H), 1.23 (s,
9 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 179.1, 149.1, 149.0, 145.4, 133.8, 132.5, 119.5, 45.3, 42.9, 35.3, 29.5, 25.6. ESI-HRMS: m/z calcd for C₁₄H₂₀ClO [M + H]⁺: 239.1197; found: 239.1185.
Compound 21b: ^¹H NMR (300 MHz, CDCl₃): δ = 7.18 (d,
1 H, J = 3.0 Hz), 6.56 (d, 1 H, J = 3.0 Hz), 5.53 (m, 1 H), 5.04 (m, 2 H), 2.33 (d, 2 H, J = 6.9 Hz), 1.27 (s, 3 H), 1.22 (s,
9 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 178.9, 153.6, 149.0, 145.1, 132.5, 126.4, 119.5, 45.1, 44.4, 35.4, 29.5, 25.5. ESI-HRMS: m/z calcd for C₁₄H₂₀BrO [M + H]⁺: 283.0692; found: 283.0688.
Compound 21c: ^¹H NMR (300 MHz, CDCl₃): δ = 7.50 (d,
1 H, J = 2.7 Hz), 6.57 (d, 1 H, J = 2.7 Hz), 5.54 (m, 1 H), 5.04 (m, 2 H), 2.32 (d, 1 H, J = 6.9 Hz), 2.29 (d, 1 H, J = 7.8 Hz), 1.27 (s, 3 H), 1.21 (s, 9 H). ^¹³C NMR (150 MHz, CDCl₃):
δ = 179.6, 161.9, 149.3, 143.8, 132.5, 119.5, 107.6, 46.1, 45.0, 35.5, 29.5, 25.3. ESI-HRMS: m/z calcd for C₁₄H₂₀IO [M + H]⁺: 331.0553; found: 331.0549.
Compound 21d: ^¹H NMR (300 MHz, CDCl₃): δ = 7.16 (d,
1 H, J = 2.7 Hz), 6.55 (1 H, d, J = 2.7 Hz), 5.47 (m, 1 H), 5.01 (m, 2 H), 2.40 (m, 2 H), 1.93 (hept, 1 H, J = 6.6 Hz), 0.93 (d, 3 H, J = 6.6 Hz), 0.89 (d, 3 H, J = 6.6 Hz). ^¹³C NMR (150 MHz, CDCl₃): δ = 179.3, 151.8, 147.4, 147.1, 132.6, 127.6, 119.1, 51.4, 41.8; 36.2, 35.7, 29.6, 18.4, 18.2. ESI-HRMS: m/z calcd for C₁₆H₂₃BrO₂Na [M + Na]⁺: 333.0824; found: 333.0822.
Compound 21e: ^¹H NMR (300 MHz, CDCl₃): δ = 7.21 (d,
1 H, J = 3.0 Hz), 6.89 (d, 1 H, J = 3.0 Hz), 5.55 (m, 1 H), 5.05 (m, 2 H), 2.33 (d, 2 H, J = 7.2 Hz), 1.27 (s, 3 H), 0.18 (s,
9 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 181.7, 162.9, 154.9, 139.6, 132.3, 125.4, 119.6, 46.0, 44.7, 25.0, -1.1. ESI-HRMS: m/z calcd for C₁₃H₁₉BrOSiNa [M + Na]⁺: 321.0280; found: 321.0278.
Compound 21f: ^¹H NMR (300 MHz, CDCl₃): δ = 7.16 (d,
1 H, J = 2.7 Hz), 6.84 (d, 1 H, J = 2.7 Hz), 5.53 (m, 1 H), 5.03 (m, 2 H), 2.35 (d, 2 H, J = 7.2 Hz), 1.65 (t, 2 H, J = 9.0 Hz), 1.25 (m, 2 H), 1.10 (m, 2 H), 0.85 (t, 3 H, J = 7.2 Hz), 0.19 (s, 9 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 182.1, 162.4, 154.3, 141.3, 132.2, 126.1, 119.4, 50.4, 44.1, 38.9, 27.2, 23.3, 14.1, -1.1. ESI-HRMS: m/z calcd for C₁₆H₂₅BrOSiNa [M + Na]⁺: 363.0750; found: 363.0752.

<A NAME="RS07408ST-19">19</A> Fleming I. Roessler F. J. Chem. Soc., Chem. Commun. 1980, 276

Analytical Data
Compound 29a: ^¹H NMR (300 MHz, CDCl₃): δ = 6.52 (s,
2 H), 2.33 (d, 2 H, J = 2.3 Hz), 2.03 (t, 1 H, J = 2.3 Hz), 1.28 (s, 3 H), 1.23 (s, 9 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.1, 146.6, 144.7, 79.8, 71.2, 38.5, 34.6, 30.9, 29.4, 25.3. ESI-HRMS: m/z calcd for C₁₈H₂₇O [M + H]⁺: 259.2056; found: 259.2042.
Compound 29h: ^¹H NMR (300 MHz, CDCl₃): δ = 6.44 (s,
2 H), 2.34 (d, 2 H, J = 2.3 Hz), 2.00 (t, 1 H, J = 2.3 Hz), 1,68 (t, 2 H, J = 8.2 Hz), 1.23 (s + q, 20 H, J = 8.2 Hz), 1.00 (sext, 2 H, J = 8.2 Hz), 0.84 (t, 3 H, J = 8.2 Hz). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.5, 148.1, 143.8, 79.7, 71.1, 42.3, 38.3, 34.8, 30.2, 29.4, 26.5, 22.9, 13.8. ESI-HRMS: m/z calcd for C₂₁H₃₃O [M + H]⁺: 301.2526; found: 301.2533.
Compound 29i: ^¹H NMR (300 MHz, CDCl₃): δ = 6.44 (s,
2 H), 5,73 (m, 1 H), 4.96 (d, 1 H, J = 18.7 Hz), 4,93 (d, 1 H, J = 10.5 Hz), 2.37 (d, 2 H, J =2.3 Hz), 2.03 (t, 1 H, J = 2.3 Hz), 1.81 (t, 2 H, J = 8.2 Hz), 1.43 (t, 2 H, J = 8.2 Hz), 1.24 (s, 18 H). ^¹³C NMR (150 MHz, CDCl₃): δ = 186.4, 148.5, 143.3, 127.6, 114.8, 79.5, 71.4, 42.2, 37.7, 34.9, 30.4, 29.4, 28.8. ESI-HRMS: m/z calcd for C₂₁H₃₁O [M + H]⁺: 299.2369; found: 299.2376.