ACCEPTED MANUSCRIPT
Hd2), 3.69 (s, 3H), 3.76 (s, 3H, OMe), 3.70-3.75 (m, 2H, PhSeCH2), 3.77-3.83 (m, 1H,
Ha), 3.86-3.89 (m, 1H, Hc), 3.92-3.96 (m, 1H, He), 4.60-4.64 (m, 1H, Hb), 6.88-8.06 (m,
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13H, ArH); C (75 MHz, CDCl3) 29.8, 34.5, 55.4, 59.1, 60.8, 63.4, 64.1, 66.8, 85.8,
114.4, 117.3, 123.5, 127.5, 129.4, 131.1, 132.8, 135.4, 135.9, 140.8, 143.1, 156.1,
164.5, 169.2, 194.4, 197.7 ppm; EI-MS m/z 647.53 (M+). Anal. Calcd for
C32H28N2O8Se: C, 59.35; H, 4.36; N, 4.33 %. Found: C, 59.48; H, 4.48; N, 4.25 %.
4.5.2. 6-(1-Hydroxyindane-2,3-dione-1-yl)-6-ethoxycarbonyl-1-(4-methoxyphenyl)-3-
(phenylselenenylmethyl)octahydroazeto[2',3':3,4]pyrrolo[1,2-b]isoxazol-2-one, 9b.
(88%); Colorless solid, mp 126-128 °C; FT-IR (KBr) 3250, 1755, 1740, 1726, 1703
1
cm-1; H (300 MHz, CDCl3) δ 0.91 (t, 3H, J 7.2, 7.5 Hz, COOCH2CH3), 2.17 (s, 1H),
2.43-2.50 (m, 1H, Hd1), 2.74-2.80 (m, 1H, Hd2), 3.67-3.72 (m, 2H, PhSeCH2), 3.77 (s,
3H, OMe), 3.78-3.86 (m, 1H, Ha), 3.89-3.91 (m, 1H, Hc), 3.92-3.94 (m, 1H, He), 4.12
(q, 2H, J 6.9, 6.9 Hz, COOCH2CH3), 4.59-4.62 (m, 1H, Hb), 6.81-7.98 (m, 13H, ArH);
13C (75 MHz, CDCl3) 13.6, 29.9, 34.5, 55.4, 59.1, 60.8, 63.4, 64.1, 66.8, 85.8, 114.4,
117.3, 123.5, 127.5, 129.4, 131.1, 132.9, 135.3, 135.9, 140.9, 143.0, 156.1, 164.5,
168.9, 194.4, 197.6 ppm; EI-MS m/z 661.56 (M+). Anal. Calcd for C33H30N2O8Se: C,
59.91; H, 4.57; N, 4.23 %. Found: C, 60.02; H, 4.66; N, 4.11 %.
4.5.3.
6-(1-Hydroxyindane-2,3-dione-1-yl)-6-cyano-1-(4-methoxyphenyl)-3-
(phenylselenenylmethyl)octahydroazeto[2',3':3,4]pyrrolo[1,2-b]isoxazol-2-one, 9c.
(90%); Colorless solid, mp 122-124 °C; FTIR (KBr) 3242, 2223, 1754, 1739, 1706
1
cm-1; H (300 MHz, CDCl3) δ 2.19 (s, 1H), 2.46-2.53 (m, 1H, Hd1), 2.77-2.84 (m, 1H,
Hd2), 3.66-3.70 (m, 2H, PhSeCH2), 3.79 (s, 3H, OMe), 3.80-3.88 (m, 1H, Ha), 3.90-3.92
(m, 1H, Hc), 3.91-3.94 (m, 1H, He), 4.58-4.62 (m, 1H, Hb), 6.86-8.14 (m, 13H, ArH);
13C (75 MHz, CDCl3) 29.9, 34.5, 55.5, 59.2, 63.4, 64.1, 66.9, 85.9, 114.6, 117.4, 120.1,
123.5, 127.5, 129.6, 131.1, 132.8, 135.4, 135.4, 140.9, 143.2, 156.1, 164.4, 194.4,197.6
ppm; EI-MS m/z 614.51 (M+). Anal. Calcd for C31H25N3O6Se: C, 60.59; H, 4.10; N,
6.84 %. Found: C, 60.68; H, 4.01; N, 6.98 %.
4.6. General procedure for the synthesis of cycloadducts, 11a-c
The bicyclic nitrone (3a) (500 mg, 1.25 mmol) and BH adduct, 2-(3-hydroxy-2-
oxoindolin-3-yl)acrylates (6a-c) (290 mg, 1.25 mmol) was added in ACI/EG (10 mL)
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