Molecules 2015, 20
75 MHz, CDCl
8493
(
3
) δ: 200.0, 170.1, 169.4, 143.0, 137.4, 132.6, 131.9, 129.7, 129.3, 128.8, 128.0, 124.4,
+
1
7
21.6, 71.7, 62.5, 45.1, 37.2, 24.8, 14.0; MS (ESI): m/z = 352 (M+H) . Anal. calcd for C21
H
21NO C,
4
1.78; H, 6.02; N, 3.99, found C, 71.90; H, 6.12; N, 3.87; Chiral HPLC: ODH column, hexane–iPrOH
(
4:1), f: 0.6 mL/min., t: 21.4 min and 23.6 min.
Ethyl 2-butyl-1-(3-methoxy-3-oxopropyl)-3-oxoisoindoline-1-carboxylate (6f). Yield: 26 mg (75%);
2
0
1
[
(
α]
m, 3H), 4.19–4.08 (m, 2H), 3.55 (s, 3H), 3.47–3.32 (m, 2H), 2.94–2.84 (m, 1H), 2.62–2.51 (m, 1H),
.95–1.83 (m, 1H), 1.73–1.62 (m, 3H), 1,4 (q, 2H, J = 7.3 Hz), 1.15 (t, 3H, J = 7.1 Hz). 0.92 (t, 3H,
D
= −25.3 (0.7 M, CHCl
3
); ee: 50%; H-NMR (250 MHz, CDCl ) δ: 7.82 (d, 1H, J = 6.5 Hz), 7.54–7.40
3
1
1
3
J = 7.1 Hz); C-NMR (60 MHz, CDCl
3
) δ: 172.6, 170.2, 169.1, 142.5, 132.1, 131.9, 129.2, 123.7,
+
1
21.4, 71.3, 62.2, 51.6, 41.5, 30.3, 27.5, 27.4, 20.5, 13.7, 13.6; MS (ESI): m/z = 348 (M+H) . Anal.
calcd for C19
H
25NO C, 65.69; H, 7.25; N, 4.03; found C, 65.80; H, 7.40; N, 4.09; Chiral HPLC: ODH
5
column, hexane–iPrOH (4:1), flow: 0.6 mL/min, t: 29.2 min and 33.7 min.
2
D
0
Ethyl 2-butyl-3-oxo-1-(3-oxobutyl)isoindoline-1-carboxylate (6g). Yield: 31 mg (95%); [α]
= −1.4
1
(
0.1 M CHCl
3
); ee: 76%; H-NMR (400 MHz, CDCl
3
) δ: 7.84 (d, 1H, J = 7.4 Hz), 7.56–7.47 (m, 2H),
7.40 (d, 1H, J = 7.1 Hz), 4.18–4.09 (m, 2H), 3.44–3.36 (m, 1H), 3.34–3.31 (m, 1H), 2.86–2.78 (m,
1
H), 2.54–2.47 (m, 1H), 2.03–1.94 (m, 1H), 1.75 (s, 3H), 1.73–1.68 (m, 2H), 1.61–1.55 (m, 1H), 1.39
1
3
(q, 2H, J = 7.5 Hz), 1.16 (t, 3H, J = 7.1 Hz), 0.94 (t, 3H, J = 7.3 Hz); C-NMR (100 MHz, CDCl
3
) δ:
2
2
06.6, 170.2, 169.1, 142.8, 132.1, 132.0, 129.2, 123.6, 121.6, 71.3, 62.1, 41.5, 36.4, 30.3, 29.9, 25.9,
+
0.5, 13.8, 13.6; MS (ESI): m/z = 332 (M+H) . Anal. calcd for C19
H
25NO C, 68.86; H, 7.60; N, 4.23;
4
C, 68.94; H, 7.75; N, 4.15; Chiral HPLC: IA-3 column, hexane–iPrOH (4:1), f: 0.6 mL/min, t: 11.3
min and 15.9 min.
2
D
0
Ethyl 2-butyl-1-(2-cyanoethyl)-3-oxoisoindoline-1-carboxylate (6h). Yield: 29 mg (97%); [α]
= −10.1
1
(1.6 M CHCl
3
); ee: 36%; H-NMR (250 MHz, CDCl
3
) δ: 7.86–7.83 (m, 1H), 7.84–7.50 (m, 2H),
7
2
.44–7.41 (m, 1H), 4.20–4.05 (m, 2H), 3.51–3.42 (m, 1H), 3.37–3.27 (m, 1H), 2.98–2.86 (m, 1H),
.65–2.53 (m, 1H), 1.99–1.86 (m, 1H), 1.73–1.65 (m, 2H), 1.41 (q, 2H, J =7.2 Hz), 1.25 (m, 1H), 1.15
1
3
(
t, 3H, J = 7.1 Hz), 0.92 (t, 3H, J = 7.1 Hz); C-NMR (60 MHz, CDCl
3
) δ: 169.6, 168.9, 141.4, 132.5,
1
32.2, 129.9, 124.2, 121.2, 118.1, 70.7, 62.6, 60.3, 41.6, 30.5, 28.5, 20.5, 13.7, 11.0; MS (ESI):
+
m/z = 315 (M+H) . Anal. calcd for C18
H
22
N
2
3
O C, 68.77; H, 7.05; N, 8.91; C, 68.90; H, 7.14; N, 8.82;
Chiral HPLC: IE-3 column, hexane–iPrOH (4:1), f: 0.6 mL/min. t: 10.0 min and 11.4 min.
2
D
0
Ethyl 3-oxo-1-(3-oxobutyl)isoindoline-1-carboxylate (6i). Yield: 25 mg (97%); [α]
= −0.3 (0.5 M
1
CHCl
3
); ee: 20%; H-NMR (400 MHz, CDCl
3
) δ: 7.82 (d, 1H, J = 7.28 Hz), 7.63–7.51 (m, 3H), 6.68
(
brs, 1H), 4.22 (q, 2H, J = 6.6 Hz), 2.56–2.25 (m, 2H), 2.19–2.12 (m, 2H), 2.03 (s, 3H), 1.26 (t, 3H,
1
3
J = 7.1 Hz);. C-NMR (100 MHz, CDCl
3
) δ: 206.8, 170.3, 169.8, 144.1, 132.6, 131.0, 129.3, 123.8,
+
1
6
23.3, 67.0, 62.4, 37.1, 30.9, 29.9, 13.9; MS (ESI): m/z = 276 (M+H) . Anal. calcd for C15
H
17NO C,
4
5.44; H, 6.22; N, 5.09; C, 65.54; H, 6.34; N, 5.15; Chiral HPLC: IA3 column, hexane–iPrOH (4:1),
flow 0.6 mL/min. t: 19.2 min and 29.4 min.
Ethyl 2,3,5,9b-tetrahydro-3-hydroxy-5-oxo-1H-pyrrolo[2,1-a]isoindole-9b-carboxylate (6j). Yield: 26 mg
2
D
0
1
(
99%); [α]
= −0.1 (1 M CHCl
3
); ee: 5%; H-NMR (300 MHz, CDCl ) δ: 7.77 (d, 1H, J = 7.1 Hz),
3