1199
A. Pejović et al.
Letter
Synlett
References and Notes
3.91 (ddt, J = 13.5, 4.3, 2.3 Hz, 1 H), 3.49 (ddd, J = 13.5, 12.7, 2.9
Hz, 1 H), 2.02 (dddd, J = 13.1, 12.7, 11.2, 4.3 Hz, 1 H), 1.78 (ddt,
J = 13.1, 2.9, 2.4 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 148.9,
129.1, 120.5, 118.4, 88.9, 81.3, 76.0, 68.6, 68.0, 67.8, 67.3, 66.0,
49.9, 29.2. MS (ES+): m/z = 348.1 [MH+]. Column chromatogra-
phy (SiO2): hexane–EtOAc, 8:2 (v/v). ESI-HRMS: m/z calcd for
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C
20H22FeNO [M + H]+: 348.1050; found: 348.1041.
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Yield 64%, yellow solid; mp 148 °C. 1H NMR (400 MHz, CDCl3): δ
= 7.43–7.38 (m, 2 H), 7.37–7.33 (m, 2 H), 7.29–7.24 (m, 1 H),
5.31 (dd, J = 9.5, 3.0 Hz, 1 H), 4.36 (ca. dt, J = 2.5, 1.3 Hz, 1 H),
4.28 (ca. dt, J = 2.5, 1.3 Hz, 1 H), 4.23–4.19 (m, 2 H), 4.24 (s, 5 H),
3.81 (ddd, J = 11.7, 10.2, 4.9 Hz, 1 H), 3.70 (ddd, J = 11.7, 5.5, 4.1
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152.8, 143.1, 129.4, 126.9, 126.0, 86.3, 76.2, 69.1, 68.5, 68.4,
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(10) 6-Ferrocenyl-3-phenyl-1,3-oxazinane (6a)
(21) 4-Ferrocenyl-3-isopropyl-1-phenyltetrahydropyrimidin-2-
one (10a)
Yield 78%, dark yellow solid; mp 86 °C. 1H NMR (400 MHz,
CDCl3): δ = 7.34–7.27 (m, 2 H), 7.13–7.09 (m, 2 H), 6.93–6.87
(m, 1 H), 5.30 (dd, J = 10.7, 2.3 Hz, 1 H), 4.74 (d, J = 10.7 Hz, 1 H),
4.48 (dd, J = 11.2, 2.4 Hz, 1 H), 4.22 (ca. dt, J = 2.5, 1.3 Hz, 1 H),
4.17 (ca. dt, J = 2.5, 1.3 Hz, 1 H), 4.15–4.07 (m, 2 H), 4.12 (s, 5 H),
Yield 61%, orange liquid. 1H NMR (400 MHz, CDCl3): δ = 7.34–
7.27 (m, 2 H), 7.25–7.20 (m, 2 H), 7.16–7.09 (m, 1 H), 4.46 (t, J =
3.9 Hz, 1 H), 4.24 (d × t, J = 2.4, 1.2 Hz, 1 H), 4.20–4.09 (m, 3 H),
4.16 (s, 5 H), 4.13–4.10 (m, 1 H), 3.62–3.46 (m, 2 H), 2.33–2.15
© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 1195–1200