C. Chithiraikumar et al.
1H), 7.69 (d, 2H, J = 8.55 Hz), 7.33 (d, 3H, J = 8.49 Hz), 7.25 (d, 3H, J = 8.94 Hz),
7.15 (d, 1H, J = 8.16 Hz), 7.14 (d, 1H, J = 7.53 Hz), 7.02 (t, 1H, J = 7.50 Hz), 4.84
(d, 1H, J = 11.31 Hz), 4.30–4.23 (m, 1H), 4.00 (t, 1H, J = 10.54 Hz), 2.75–2.59
(m, 2H), 2.07–1.90 (m, 2H), 1.77–1.66 (m, 2H). 13C NMR (75 MHz, CDCl3) δC
196.13, 180.97, 147.94, 147.54, 141.03, 135.86, 131.91, 130.18, 129.70, 129.42,
128.77, 127.77, 125.01, 124.35, 122.87, 110.71, 73.74, 72.10, 65.23, 53.17, 48.50,
30.81, 27.49; ESI Mass: m/z [M + H+]: 534.08.
2′‑Benzoyl‑1′‑(2,4‑difluorophenyl)‑1′,2′,5′,6′,7′,7a’‑hexahydrospiro[indoline
‑3,3′‑pyrrolizin]‑2‑one (8m) White solid (98% yield). m.p. 125–127 °C; 72%
ee’s, determined by HPLC [Chiralcel OD-H, n-hexane/i-propanol = 80/20, 1 ml/
min, λ = 254 nm, t (major) = 3.49 min, t (minor) = 16.97 min]. [α]D25 = – 100.1°
1
(c = 1.29, CHCl3); H NMR (300 MHz, CDCl3) δH 7.66 (s, 1H), 7.54–7.46 (m,
2H), 7.41–7.33 (m, 4H), 7.24–7.12 (m, 3H), 7.10 (d, 1H, J = 7.14 Hz), 7.02 (t,
1H, J = 7.42 Hz), 6.88–6.77 (m, 2H), 6.53 (d, 1H, J = 7.56 Hz), 5.04 (d, 1H,
J = 11.34 Hz), 4.22–4.16 (m, 2H), 2.68–2.57 (m, 2H), 2.05–1.97 (m, 2H), 1.93–
1.74 (m, 2H). 13C NMR (75 MHz, CDCl3) δC 196.65, 180.95, 140.60, 136.68,
132.81, 129.62, 129.36, 127.92, 127.64, 127.10, 124.69, 122.19, 111.51, 111.23,
110.15, 104.00, 103.66, 73.42, 70.81, 62.58, 47.98, 45.53, 30.49, 27.07; ESI Mass:
m/z [M + H+]: 446.19.
2′‑(3‑Bromobenzoyl)‑1′‑(2,4‑difuorophenyl)‑1′,2′,5′,6′,7′,7a’‑hexahydro spiro[
indoline‑3,3′‑pyrrolizin]‑2‑one (8n) White solid (99% yield). m.p. 135–137 °C;
75% ee’s, determined by HPLC [Chiralcel OD-H, n-hexane/i-propanol = 80/20,
1 ml/min, λ = 254 nm, t (major) = 3.39 min, t (minor) = 12.42 min]. [α]D25 = – 51.7°
1
(c = 1.31, CHCl3); H NMR (300 MHz, CDCl3) δH 8.44 (s, 1H), 7.46 (t, 2H,
J = 6.54 Hz), 7.32–7.21 (m 5H), 7.13 (t, 2H, J = 7.57 Hz), 7.00 (t, 3H, J = 8.34 Hz),
6.62 (d, 1H, J = 7.68 Hz), 4.80 (d, 1H, J = 11.40 Hz), 4.23–4.16 (m, 1H), 3.87
(t, 1H, J = 10.59 Hz), 2.68–2.61 (m, 2H), 2.04–1.87 (m, 2H), 1.76–1.65 (m, 2H).
13C NMR (75 MHz, CDCl3) δC 196.04, 181.32, 163.50, 160.26, 140.81, 135.61,
131.45, 129.65, 129.50, 129.39, 128.26, 127.42, 122.38, 115.74, 115.46, 110.54,
73.74, 71.95, 64.49, 52.25, 48.29, 30.63, 27.25; ESI Mass: m/z [M+]: 524.09.
2′‑Benzoyl‑1′‑(2‑methoxyphenyl)‑1′,2′,5′,6′,7′,7a’‑hexahydrospiro[indolin
e‑3,3′‑pyrrolizin]‑2‑one (8o) White solid (94% yield). m.p. 120–122 °C; 96%
ee’s, determined by HPLC [Chiralcel OD-H, n-hexane/i-propanol = 80/20, 1 ml/
min, λ = 254 nm, t (major) = 20.07 min, t (minor) = 28.28 min]. [α]D25 = – 73.5°
1
(c = 1.21, CHCl3); H NMR (300 MHz, CDCl3) δH 8.11 (s, 1H), 7.47–7.39 (m,
4H), 7.32 (t, 2H, J = 2.86 Hz), 7.16 (d, 2H, J = 7.14 Hz), 7.09–7.00 (m 2H), 6.93–
6.86 (m, 2H), 6.56 (d, 1H, J = 7.53 Hz), 5.33 (d, 1H, J = 10.50 Hz), 4.29 (t, 2H,
J = 10.14 Hz), 3.93 (s, 3H), 2.67–2.61 (m, 2H), 1.99–1.85 (m, 4H). 13C NMR
(75 MHz, CDCl3) δC 197.25, 181.25, 157.85, 140.62, 137.14, 132.52, 129.08,
128.63, 127.83, 127.65, 127.44, 127.31, 125.24, 122.02, 120.64, 110.97, 109.98,
73.70, 70.62, 61.62, 55.50, 48.01, 47.39, 30.81, 27.22; ESI Mass: m/z [M + H+]:
440.23.
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