10.1002/chem.201904930
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Procedure for the synthesis of [10+2] cycloadduct 3b.
(E)-2-Benzylidene-6-nitro-1-indanone 1b (31.8 mg, 0.12 mmol), 3-olefinic
oxindole 2a (23.1 mg, 0.10 mmol), PTC C8 (0.6 mg, 0.001 mmol), and
Cs2CO3 (13.0 mg, 0.04 mmol) were added to a test tube followed by the
addition of toluene (2.0 mL). The mixture was stirred at room temperature
overnight, and monitored by TLC. After completion, the product 3b was
obtained by flash chromatography on silica gel (EtOAc/petroleum ether =
1/10–1/8): White solid, 48.6 mg, 94% yield; mp: 137140 C; >19:1 dr;
95% ee, determined by HPLC analysis [Daicel Chiral IA (n-hexane/iPrOH
= 60/40), 1.0 mL/min, λ = 254 nm, t (major) = 16.30 min, t (minor) = 21.25
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25
1
min]; [α]D = +49.5 (c = 0.11, CHCl3); H NMR (400 MHz, CDCl3) δ (ppm)
8.58 (d, J = 2.1 Hz, 1H), 8.52 (dd, J = 8.4, 2.2 Hz, 1H), 7.86 (d, J = 8.4
Hz, 1H), 7.39 (d, J = 7.2 Hz, 1H), 7.21 (td, J = 7.8, 0.9 Hz, 1H), 7.10–7.01
(m, 4H), 6.95 (dd, J = 7.8, 1.3 Hz, 2H), 6.59 (d, J = 7.8 Hz, 1H), 4.97 (t, J
= 8.9 Hz, 1H), 4.12 (dd, J = 11.7, 8.8 Hz, 1H), 3.93 (dq, J = 10.7, 7.1 Hz,
1H), 3.78 (d, J = 11.8 Hz, 1H), 3.72 (dq, J = 10.7, 7.1 Hz, 1H), 3.67 (d, J
= 9.0 Hz, 1H), 3.02 (s, 3H), 0.68 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm) 202.0, 175.7, 170.3, 161.0, 148.8, 143.7, 136.7, 133.7,
130.0, 129.1, 127.9, 127.9, 127.8, 127.7, 126.5, 124.0, 122.4, 112.0,
108.2, 66.5, 61.2, 56.5, 56.1, 54.5, 45.5, 26.3, 13.4; HRMS (ESI): Calcd.
for C29H25N2O6+ ([M+H]+): 497.1707, found: 497.1707.
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Acknowledgements
We are grateful for the financial support from the NSFC
(20961132004 and 21772126).
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Keywords: higher-order cycloaddition • isobenzofulvene • [10+2]
cycloaddition • phase-transfer catalysis • chemoselectivity
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