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2O and chromatographic purification of the crude product on silica gel gave the homoallylic alcohol 1a in 92% yield.
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2O and chromatographic purification of the crude product on silica gel gave the homoallylic alcohol 1a in 92% yield.
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46
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38549182168
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Selected spectroscopic data: Compound 1a:20 1H NMR (400 MHz, CDCl3, δ, 2.13 (br s, 1 H, 2.47-2.52 (m, 2 H, 4.72 (t, J, 6.5 Hz, 1 H, 5.11-5.19 (m, 2 H, 5.76-5.85 (m, 1 H, 7.25-7.29 (m, 1 H, 7.32-7.35 (m, 4 H, Compound 1b:10 1H NMR (400 MHz, CDCl3, δ, 2.15 (br s, 1 H, 2.43-2.52 (m, 1 H, 2.54-2.62 (m, 1 H, 4.85-4.89 (m, 1 H, 5.18-5.22 (m, 2 H, 5.75-5.84 (m, 1 H, 7.53 (t, J, 8.0 Hz, 1 H, 7.70 (d, J, 7.6 Hz, 1 H, 8.14 (d, J, 8.1 Hz, 1 H, 8.25 (s, 1 H, Compound 1c:10 1H NMR (400 MHz, CDCl3, δ, 2.48-2.63 (m, 2 H, 2.82 (br s, 1 H, 4.90 (t, J, 6.2 Hz, 1 H, 5.17-5.22 (m, 2 H, 5.77-5.87 (m, 1 H, 7.56 (d, J, 8.0 Hz, 2 H, 8.21 (d, J, 8.0 Hz, 2 H, Compound 1d:21 1H NMR (400 MHz, CDCl3, δ, 2.45-2.49 (m, 2 H, 3.77 s, 3 H, 4
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3): δ = 1.36 (s, 3 H), 1.43 (s, 3 H), 2.16-2.24 (m, 1 H), 2.25-2.37 (m, 1 H), 2.41 (brs, 1 H, OH), 3.62-3.78 (m, 1 H), 3.90-3.95 (m, 1 H), 3.98-4.06 (m, 2 H), 5.10-5.17 (m, 2 H), 5.80-5.91 (m, 1 H).
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