Synthesis of 8-Oxabicyclo[3.2.1]octanes by TiCl4-Mediated Reactions of 3-Alkoxycyclobutanones and Allenylsilanes

Tatsuo Onnagawa; Mizuki Yamazaki; Tomoyuki Yoshimura; Jun-ichi Matsuo

doi:10.1055/s-0037-1611276

Synlett, Table of Contents

Synlett 2018; 29(20): 2717-2721
DOI: 10.1055/s-0037-1611276

letter

Synthesis of 8-Oxabicyclo[3.2.1]octanes by TiCl₄-Mediated Reactions of 3-Alkoxycyclobutanones and Allenylsilanes

Tatsuo Onnagawa

,

Mizuki Yamazaki

,

Tomoyuki Yoshimura

,

Jun-ichi Matsuo*

Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Email: jimatsuo@p.kanazawa-u.ac.jp

› Author Affiliations

Abstract

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Abstract

1-Substituted allenylsilanes reacted with 3-alkoxycyclobutanones in the presence of TiCl₄ to afford 8-oxabicyclo[3.2.1]octan-3-ones stereoselectively. Nucleophilic attack of allenylsilanes to a 1,4-zwitterionic intermediate formed from 3-alkoxycyclobutanones and TiCl₄ followed by 1,2-silyl migration, five-membered cyclization with an alkoxy group, and seven-membered cyclization of titanium enolate was proposed. Deuteration and one-pot Peterson olefination suggested that alkyl titanium species were formed after cyclization to 8-oxabicyclo[3.2.1]octane skeletons.

Key words

cyclobutanone - allenylsilane - Lewis acid - 8-oxabicyclo[3.2.1]octane - alkyl titanium bond

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References

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28 Typical Experimental Procedure for TiCl₄-Mediated Reaction of Cyclobutanone 5a and Allenylsilane 1a to 8-Oxabicyclo[3.2.1]octan-3-one (9a) To a stirred solution of 1a (51.9 mg, 0.18 mmol) and 5a (40.4 mg, 0.28 mmol) in dry toluene (1.0 mL) was added TiCl₄ (1.0 M solution in CH₂Cl₂, 0.28 mL, 0.28 mmol) at –45 °C, and the mixture was stirred for 2 h at the same temperature. The reaction was quenched by adding aqueous solution of potassium sodium (+)-tartrate, and the resulting mixture was extracted with ethyl acetate (three times). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (6.8 g, hexane/ethyl acetate = 6:1) to afford 9a (48.4 mg, 0.12 mmol, 67%) and 10a (2.2 mg, 5.4 μmol, 3%). Compound 9a: mp 202.5–203.0 °C. ¹H NMR (600 MHz, CDCl₃): δ = 7.88–7.87 (2 H, m), 7.55 (2 H, d, J = 7.8 Hz), 7.45–7.43 (3 H, m), 7.35 (1 H, t, J = 7.5 Hz), 7.29 (2 H, t, J = 7.5 Hz), 4.80 (1 H, t, J = 6.0 Hz), 2.97 (1 H, ddd, J = 14.7, 6.0, 1.5 Hz), 2.69–2.63 (1 H, m), 2.21 (1 H, d, J = 14.7 Hz), 2.14–2.09 (2 H, m), 1.11 (3 H, s), 1.00 (9 H, s), 0.96 (3 H, s), 0.86 (3 H, s). ¹³C NMR (150 MHz, CDCl₃): δ = 212.9, 136.7, 135.8, 135.5, 132.7, 129.2, 129.1, 127.9, 127.6, 88.5, 74.5, 57.1, 45.3, 36.0, 29.3, 28.0, 22.4, 19.5, 19.3, 18.9. IR (CHCl₃): 3072, 3054, 3010, 2967, 2933, 2859, 1706, 1589, 1469, 1427, 1392, 1272, 1105, 1035 cm^–1. HRMS (DART+): m/z [M + H]⁺ calcd for C₂₆H₃₅O₂Si: 407.24063; found: 407.24038. Compound 10a: ¹H NMR (600 MHz, CDCl₃): δ = 7.62–7.60 (4 H, m), 7.39–7.33 (6 H, m), 4.99–4.94 (1 H, m), 3.19 (1 H, ddq, J = 15.0, 9.6, 1.8 Hz), 3.02 (1 H, dd, J = 16.8, 6.6 Hz), 2.72 (1 H, dd, J = 15.0, 6.3 Hz), 2.68–2.61 (1 H, m), 2.55 (1 H, ddq, J = 16.8, 7.4, 1.8 Hz), 1.31 (3 H, t, J = 1.5 Hz), 1.13 (3 H, d, J = 1.2 Hz), 1.12 (3 H, d, J = 1.8 Hz), 1.07 (9 H, s). ¹³C NMR (150 MHz, CDCl₃): δ = 212.5, 163.6, 136.0, 135.9, 135.5, 135.3, 129.0, 127.6, 94.3, 76.5, 46.5, 42.4, 41.4, 29.7, 28.1, 18.9, 18.0, 17.9, 15.3. IR (CHCl₃): 3072, 3018, 2965, 2931, 2857, 1708, 1623, 1469, 1427, 1261, 1209, 1103 cm^–1. HRMS (DART+): m/z [M + H]⁺ calcd for C₂₆H₃₅O₂Si: 407.24063; found: 407.24053.

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