8727
13. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
1
14. Characterization data for new compounds: Compound 5: H NMR (360 MHz, CDCl3) l 7.42–7.0 (m, 10H), 5.28
(m, 2H), 1.98–1.80 (m, 2H), 1.74–1.60 (m, 2H), 1.30–1.17 (m, 2H), 1.16–1.10 (m, 2H); 13C NMR (90 MHz,
CDCl3) l 147.5, 131.0, 128.3, 125.7, 125.6, 26.6, 25.1, 16.7. HRMS (M+) m/z calcd for C20H20 260.1565, found
260.1559. Compound 9: [h]D=−107.0 (c 0.0242, CH2Cl2); 1H NMR (360 MHz, CDCl3) l 3.49–3.35 (m, 4H), 0.90
(s, 9H), 0.90 (m, 1H), 0.89–0.78 (m, 1H), 0.77–0.63 (m, 3H), 0.62–0.48 (m, 4H), 0.31–0.17 (m, 4H), 0.15–0.03 (m,
4H), 0.05 (s, 6H); 13C NMR (90 MHz, CDCl3) l 67.0, 66.7, 26.0, 19.7, 19.5, 18.6, 18.4 (2), 18.1 (2), 18.0, 8.3 (3),
1
8.25, 0.01, −5.1. Compound 11: H NMR (360 MHz, CDCl3) l 5.36 (ddd, 1H, J=17.1, 10.3, 9.7 Hz), 4.99 (d,
1H, J=17.1 Hz), 4.80 (d, 1H, J=10.3 Hz), 3.49–3.38 (m, 2H), 1.21–1.10 (m, 1H), 0.90 (s, 9H), 0.89–0.80 (m, 1H),
0.79–0.62 (m, 3H), 0.61–0.50 (m, 5H), 0.49–0.40 (m, 2H), 0.28–0.18 (m, 2H), 0.15–0.02 (m, 2H), 0.05 (s, 6H); 13C
NMR (90 MHz, CDCl3) l 141.9, 111.1, 66.7, 26.0, 22.3, 21.2, 19.5, 18.6, 18.4, 18.2 (2), 18.1, 11.8, 8.2, 8.1, 7.8,
0.01, −5.1. HRMS (MH+) m/z calcd for C21H37OSi 333.2614, found 333.2608. Compound 12: 1H NMR (360
MHz, CDCl3) l 7.40–7.03 (m, 5H), 5.17 (dd, 1H, J=15.2, 7.8 Hz), 5.08 (dd, J=15.2, 8.0 Hz), 3.55–3.35 (m, 2H),
1.98–1.68 (m, 1H), 1.66–1.54 (m, 1H), 1.21–1.00 (m, 2H), 0.90 (s, 9H), 0.95–0.31 (m, 11H), 0.30–0.18 (m, 1H),
0.18–0.02 (m, 4H), 0.05 (s, 6H); 13C NMR (90 MHz, CDCl3) l 132.5, 129.5, 128.3, 125.7, 125.5, 125.4, 66.7, 26.6,
26.0, 25.0, 22.0, 20.1, 19.5, 18.6, 18.4, 18.1 (2), 16.7, 11.6, 8.4, 8.2, 8.1, 7.8, −5.1. HRMS (MNH4+) m/z calcd for
C30H48NOSi 466.3505, found 466.3493. Compound 13: 1H NMR (360 MHz, CDCl3) l 8.15–8.00 (m, 2H),
7.61–7.52 (m, 1H), 7.50–7.41 (m, 2H), 5.45 (ddd, 1H, J=17.1, 10.1, 8.4 Hz), 5.09 (d, 1H, J=17.1 Hz), 4.91 (d,
1H, J=10.1 Hz), 4.26 (dd, 1H, J=11.5, 7.0 Hz), 4.19 (dd, 1H, J=11.5, 7.1 Hz), 1.57–1.47 (m, 1H), 1.45–1.30 (m,
1H), 0.95–0.74 (m, 2H); 13C NMR (90 MHz, CDCl3) l 166.7, 140.1, 132.9, 130.4, 129.6, 128.3, 112.8, 68.1, 20.9,
19.3, 12.0. Compound 14: [h]D=−13.77 (c 0094, CH2Cl2); 1H NMR (360 MHz, CDCl3) l 8.13–8.00 (m, 4H),
7.62–7.51 (m, 2H), 7.50–7.40 (m, 4H), 5.18 (m, 2H), 4.29–4.20 (m, 2H), 4.18–4.12 (m, 2H), 1.46–1.38 (m, 2H),
1.33–1.23 (m, 2H), 0.85–0.63 (m, 4H); 13C NMR (90 MHz, CDCl3) l 166.7, 132.9, 131.2, 130.5, 129.6, 128.3, 68.3,
19.8, 19.1, 11.9. HRMS (MNH+) m/z calcd for C24H28NO4 394.2018, found 394.2024. Compound 15: [h]D=
1
−109.38 (c 0.00256, CDCl3); H NMR (360 MHz, CDCl3) l 8.12–8.01 (m, 2H), 7.60–7.51 (m, 1H), 7.50–7.41 (m,
2H), 5.1 (m, 2H), 4.34–4.21 (m, 1H), 4.19–4.08 (m, 1H), 3.52–3.38 (m, 2H), 1.67–1.53 (m, 1H), 3.52–3.38 (m, 1H),
1.35–1.20 (m, 3H), 1.10–1.01 (m, 1H), 0.98–0.66 (m, 5H), 0.89 (s, 9H), 0.65–0.48 (m, 3H), 0.43–0.32 (m, 2H),
0.30–0.05 (m, 4H), 0.04 (s, 6H); 13C NMR (90 MHz, CDCl3) l 166.7, 132.8, 132.3, 130.5, 129.6, 128.9, 128.3,
68.4, 66.7, 26.0, 21.9, 20.9, 20.0, 19.8, 19.5, 19.0, 18.6, 18.4, 18.1 (2), 11.8, 11.5, 8.2, 8.1, 7.7, 0.01, −5.1. HRMS
(MNH+) m/z calcd for C32H47NO3Si 507.3295, found 507.3289.
15. McDonald, W. S.; Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 1997, 62, 1215.
16. We can offer no rationalization for this observation that the isolated yield appears to be higher than predicted
by simple statistical analysis.
17. Separation of diastereomers was attempted by column chromatography, although removal of all diastereomeric
side products was not possible.
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18. Assignment made by comparison to optical rotation and H and 13C-characterization data reported in Ref. 5c.
.