KUMAR ET AL.
9
298 K, CDCl3) δ 7.30–7.28 (m, 1H), 7.16–7.15 (m, 4H),
7.08 (dd, J = 9.5, J = 1.4 Hz, 1H), 7.06–7.02 (m, 1H),
6.80–6.78 (m, 2H), 6.76–6.74 (m, 2H), 6.61–6.59 (m,
2H), 6.44–6.42 (m, 1H), 4.86 (d, J = 16.0 Hz, 1H), 4.71
(d, J = 10.8 Hz, 1H), 4.66 (d, J = 16.0 Hz, 1H), 4.37
(d, J = 10.8 Hz, 1H), 3.72 (s, 3H), 3.15 (d, J = 2.0 Hz,
2H), 1.87 (s, 3H); 13C NMR (100 MHz, sw = 15 ppm,
scans = 1024, 298 K, CDCl3) δ 176.8, 170.4, 158.4,
143.1, 135.1, 131.1, 131.1, 128.7, 128.4, 128.4, 127.2,
126.6, 126.6, 123.8, 122.2, 113.3, 109.2, 67.37, 55.03,
54.32, 43.43, 38.69, 20.6; Enantiomeric excess: 99%,
determined by HPLC (Daicel chiralpak IA, hexane/i-
PrOH, 90:10, flow rate 1.0 mL/min, λ = 254 nm):
Retention times were: for (R)-3g, 15.1 min (major); for
(S)-3g, 17.7 min (minor); ESI-HRMS calcd for
C26H25NO4 [M + H]+ 416.1856, found 416.1890.
scans = 1024, CDCl3) δ 170.3, 143.2, 133.2, 132.4, 132.3,
128.9, 128.6, 128.5, 128.2, 128.2, 127.8, 127.3, 127.0, 126.4,
125.8, 125.6, 124.0, 122.3, 109.2, 67.5, 54.36, 43.15, 39.62,
20.60; Enantiomeric excess: 98%, determined by HPLC
(Daicel chiralpak IA, hexane/i-PrOH, 90:10, flow rate
0.5 mL/min, λ = 254 nm): Retention times were: for
(R)-3i, 28.16 min (major); for (S)-3i, 43.99 min (minor);
ESI-HRMS calcd for C24H21NO3 [M + H]+ 436.1907,
found 436.1943.
2.6.31 | (R)-(1-Allyl-3-benzyl-
2-oxoindolin-3-yl)methyl acetate (3j)
25
Colorless semi-solid; [α]D
= −60.9 (c = 0.1 in
1
CHCl3); H NMR (500 MHz, sw = 20 ppm, scans = 16,
298 K, CDCl3) δ 7.26 (d, J = 2.1 Hz, 1H), 7.21–7.16
(m, 1H), 7.11–7.01 (m, 4H), 6.89–6.82 (m, 2H), 6.59 (d,
J = 7.8 Hz, 1H), 5.44 (ddt, J = 17.1, J = 10.1,
J = 4.9 Hz, 1H), 4.96 (dd, J = 10.4, J = 1.0 Hz, 1H),
4.69 (d, J = 10.8 Hz, 2H), 4.35 (d, J = 10.8 Hz, 1H),
4.26–4.19 (m, 1H), 4.10–4.03 (m, 1H), 3.17 (d,
J = 13.0 Hz, 1H), 3.13 (d, J = 5.9 Hz, 1H), 1.88 (s,
3H); 13C NMR (125 MHz, sw = 236 ppm, scans = 1024,
CDCl3) δ 176.3, 170.3, 143.2, 134.6, 130.7, 130.0, 129.9,
128.5, 128.3, 127.7, 127.6, 126.7, 124.0, 123.9, 122.1,
108.9, 108.1, 67.06, 54.08, 41.90, 39.75, 20.60, 11.19;
Enantiomeric excess: 56%, determined by HPLC
(Daicel chiralpak IA, hexane/i-PrOH, 95:5, flow rate
1.0 mL/min, λ = 254 nm): Retention times were: for
(S)-3j, 10.49 min (minor); for (R)-3j, 11.68 min (major);
ESI-HRMS calcd for C21H21NO3 [M + H]+ 336.1594,
found 336.1603.
2.6.29 | (R)-(3-Allyl-1-benzyl-
2-oxoindolin-3-yl)methyl acetate (3h)
25
Colorless semi-solid; [α]D = −39.9 (c = 0.1 in CHCl3);
1H NMR (500 MHz, sw = 20 ppm, scans = 16, 298 K,
CDCl3) δ 7.29–7.23 (m, 6H), 7.17 (t, J = 7.5 Hz, 1H), 7.03
(t, J = 7.5 1H), 6.70 (d, J = 8.0 Hz, 1H), 5.49–5.41 (m,
1H), 5.09–5.05 (m, 1H), 4.97 (d, J = 16.0 Hz, 1H), 4.80 (d,
J = 16.0 Hz, 1H), 4.63 (d, J = 10.5 Hz, 1H), 4.18 (d,
J = 10.5 Hz, 1H), 2.63 (d, J = 7.0 Hz, 2H), 1.83 (s, 3H);
13C NMR (125 MHz, sw = 236 ppm, scans = 1024,
CDCl3) δ 177.1, 170.3, 143.1, 135.7, 131.0, 129.0, 128.6,
128.4, 127.5, 127.2, 123.5, 122.5, 119.7, 109.1, 67.09, 52.34,
43.69, 38.05, 20.53; Enantiomeric excess: 93%, determined
by HPLC (Daicel chiralpak AD-H, hexane/i-PrOH, 90:10,
flow rate 1.0 mL/min, λ = 254 nm): Retention times
were: for (S)-3h, 12.17 min (minor); for (R)-3h, 19.52 min
(major); ESI-HRMS calcd for C21H21NO3 [M + H]+
336.1594, found 336.1609.
2.6.32 | (R)-(1-Allyl-3-benzyl-5-chloro-
2-oxoindolin-3-yl)methyl acetate (3k)
25
Colorless semi-solid; [α]D
= −83.9 (c = 0.2 in
1
2.6.30 | (R)-(1-Benzyl-3-(naphthalen-
2-ylmethyl)-2-oxoindolin-3-yl)methyl
acetate (3i)
CHCl3); H NMR (500 MHz, sw = 20 ppm, scans = 16,
298 K, CDCl3) δ 7.24 (d, J = 2.0 Hz, 1H), 7.16 (dd,
J = 8.0, 2.0 Hz, 1H), 7.11–7.08 (m, 3H), 6.85 (d,
J = 7.0 Hz, 2H), 6.51 (d, J = 8.5 Hz, 1H), 5.44–5.37
25
Colorless semi-solid; [α]D = −146.8 (c = 0.1 in CHCl3);
(m, 1H), 4.96 (d, J = 10.5 Hz, 1H), 4.66 (d,
1H NMR (500 MHz, sw = 20 ppm, scans = 16, 298 K,
CDCl3) δ 7.73 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 7.5 Hz,
1H), 7.50 (d, J = 8.5 Hz, 1H), 7.43–7.37 (m, 4H),
7.08–7.05 (m, 2H), 6.98 (t, J = 7.5 Hz, 1H), 6.94 (dd,
J = 8.5, J = 2.0 Hz, 1 Hz), 6.72 (t, J = 8.0 Hz, 1H), 6.54 (d,
J = 7.5 Hz, 1H), 6.37–6.33 (m, 1H), 4.85 (d, J = 16.0 Hz,
1H), 4.78 (d, J = 10.5 Hz, 1H), 4.55 (d, J = 16.0 Hz, 1H),
4.43 (d, J = 11.0 Hz, 1H), 3.38 (dd, J = 23.5, J = 13.0 Hz,
2H), 1.89 (s, 3H); 13C NMR (125 MHz, sw = 236 ppm,
J = 17.0 Hz, 1H), 4.61 (d, J = 10.5 Hz, 1H), 4.36 (d,
J = 11.0 Hz, 1H), 4.22–4.17 (m, 1H), 4.04 (dd,
J = 16.5, J = 5.0 Hz, 1H), 3.17 (dd, J = 33.5,
J = 13.0 Hz, 1H), 1.92 (s, 3H); 13C NMR (125 MHz,
sw = 236 ppm, scans = 1024, CDCl3) δ 175.8, 170.2,
141.7, 134.1, 130.5, 130.3, 129.9, 128.3, 127.9, 127.6,
126.9, 124.3, 117.0, 109.9, 66.93, 54.30, 42.05, 39.75,
20.51; Enantiomeric excess: 91%, determined by HPLC
(Daicel chiralpak IA, hexane/i-PrOH, 93:7, flow rate