NJC
Paper
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d6-DMSO): d 197.1, 166.6 160.2, 154.2, 153.3, 151.0, 137.9,
132.1, 131.0, 128.6, 127.8, 126.6, 124.7, 118.9, 116.7, 114.2,
25
111.5, 109.2, 107.8, 98.9, 34.9, 33.3, 22.2, 18.5, 14.1. [a]D
=
+224.01 (c = 0.2, THF). ESI-MS [M + 1]+: 769.20. Anal. Calcd for
C
50H44N2O6: C, 78.10; H, 5.77; N, 3.64. Found: C, 78.39; H, 6.02;
N, 3.80. FT-IR (KBr, cmꢁ1): 3425.20, 2857.51, 2429.86, 1728.49,
1590.44, 1380.21, 1132.10.
Synthesis of L2. The imine-based compound L1 (0.15 g,
0.20 mmol) was dissolved in a mixed solvent of 50 mL THF
and 5 mL MeOH. The mixed solution was stirred at room
temperature and NaBH4 was added in batches to the above
solution until the yellow colour disappeared, and then the
colourless solution was stirred for another 30 min. 10 mL
saturated NH4Cl solution was added to the mixture to quench
the reaction, and the mixture was extracted with CH2Cl2.
Combined organic layers were washed with brine, dried over
anhydrous Na2SO4, and evaporated under reduced pressure to
1
afford a pale yellow solid L2 in 81.2% yield (0.12 g). H NMR
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G. Dong, Org. Lett., 2011, 13, 1900; (c) C. M. Kizas,
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20, 575.
(300 Hz, d6-DMSO): d 8.39 (s, 1H), 7.70 (s, 1H), 7.51 (t, 2H, J =
9.0 Hz), 7.30 (t, 2H, J = 6.0 Hz), 7.04 (dd, 1H, J = 9.0, 1.2 Hz), 6.78
(d, 2H, J = 8.7 Hz), 6.48 (d, 1H, J = 1.8 Hz), 5.93 (s, 1H), 4.49–4.63
(m, 1H), 2.61 (t, 2H, J = 7.5 Hz), 2.33 (s, 2H), 1.50–1.60 (m, 2H),
1.27 (q, 3H, J = 7.5 Hz), 0.86 (t, 3H, J = 7.2 Hz). 13C NMR
(75 MHz, d6-DMSO): d 161.1, 156.0, 154.1, 153.0, 151.7, 137.1,
132.0, 128.7, 128.4, 127.4, 126.5, 126.3, 126.1, 124.5, 114.7,
111.0, 109.4, 108.0, 97.1, 42.8, 35.0, 33.5, 22.1, 18.4, 14.1.
25
[a]D = +74.21 (c = 0.2, THF). ESI-MS [M + 1]+: 773.25. Anal.
Calcd for C50H48N2O6: C, 77.70; H, 6.26; N, 3.62. Found: C,
77.69; H, 6.12; N, 3.70. FT-IR (KBr, cmꢁ1): 3413.15, 1705.06,
1612.03, 1394.82, 1155.31, 832.83.
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Acknowledgements
This work was supported by the National Natural Science
Foundation of China (No. 21074054, 21172106, 51173078),
National Basic Research Program of China (2010CB923303)
and Zhejiang Provincial Natural Science Foundation (No.
Y4110141).
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