1
3d: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.95,
390.1812 found 390.1807. HPLC (Chiralpak IB, n-hexane:
i-PrOH = 95 : 5, λ = 254 nm, 1.0 mL min−1): 15.9, 16.7, 20.9,
22.1 min.
(d, J = 8.5 Hz, 2H), 7.84, (d, J = 8.6 Hz, 2H), 7.37–7.23 (m,
4H), 7.23–7.17 (m, 1H), 3.43–3.33 (m, 2H), 2.99 (dd, J = 10.5
Hz, J′ = 19.2 Hz, 1H), 2.21 (s, 3H), 2.13–2.00 (m, 2H), 0.83 (t,
J = 7.4 Hz, 3H). 13C NMR (CDC3, 100 MHz) δ (ppm): 175.3,
174.7, 174.2, 161.9, 138.5, 135.6, 130.2, 130.1, 128.3, 127.8,
127.6 (m, CF3), 126.9, 120.3, 59.5, 44.7, 31.3, 28.2, 15.6, 9.4.
HRMS (ESI): calcd. for [M+H]+ (C23H21F3N3O3) requires
444.1530, found 444.1523. HPLC (Chiralpak IA, n-hexane:
i-PrOH = 80 : 20, λ = 254 nm, 1.0 mL min−1): tR = 12.0,
16.0 min.
1
3i: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.85
(d, J = 7.7 Hz, 2H), 7.45–7.35 (m, 3H), 7.23–7.18 (m,2H), 7.13
(d, J = 8.6 Hz, 2H), 3.39–3.24 (m, 2H), 2.96 (dd, J = 9.1 Hz, J′
= 18.3 Hz, 1H), 2.20 (s, 3H), 2.18–2.04 (m, 2H), 0.83 (m, 3H).
13C NMR (CDC3, 100 MHz) δ (ppm): 175.6, 174.9, 174.3,
161.9, 147.6, 144.7, 138.7, 137.8, 136.0, 130.8, 130.7, 130.4,
130.3, 128.9, 127.0, 59.8, 44.8, 32.3, 31.5, 28.3, 15.8, 9.5.
HRMS (ESI): calcd. for [M+H]+ (C22H21ClN3O3) requires
410.1266 found 410.1275. HPLC (Chiralpak IB, n-hexane:
i-PrOH = 90 : 10, λ = 254 nm, 1.0 mL min−1): tR = 24.6,
39.3 min.
1
3e: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.85
(d, J = 7.7 Hz, 2H), 7.40 (t, J = 7.7 Hz, 2H), 7.23–7.18 (m, 1H),
7.00 (d, J = 9.1 Hz, 2H), 3.33 (dd, J = 5.6 Hz, J′ = 9.3 Hz, 1H),
3.11–3.01 (m, 1H), 3.00–2.85 (m, 1H), 2.93 (s, 6H), 2.18 (s,
3H), 2.17–2.00 (m, 2H), 0.81 (t, J = 7.4 Hz, 3H). 13C NMR
(CDC3, 100 MHz) δ (ppm): 176.4, 175.9, 174.5, 161.9, 151.9,
138.8, 130.3, 128.3, 126.9, 120.6, 113.8, 60.4, 44.5, 41.8, 31.6,
28.2, 16.0, 9.5. HRMS (ESI): calcd. for [M+H]+ (C26H33N4O3)
requires 449.2547 found 449.2558. HPLC (Chiralpak IA,
1
3j: White scum (mixture of diastereomers). H NMR (CDCl3,
400 MHz) δ (ppm): 7.90–7.85 (m, 4H), 7.45–7.35, (m, 4H),
7.30–7.15 (m, 8H), 7.02–6.96 (m, 1H), 6.88–6.84 (m, 1H), 3.75
(dd, J = 5.4 Hz, J′ = 18.0 Hz, 1H), 3.43–3.34 (m, 2H),
3.25–3.16 (m, 1H), 3.05–2.93 (m, 2H), 2.24 (s, 3H), 2.21 (s,
3H), 2.15–2.05 (m, 1H), 2.11 (s, 3H), 1.95–1.85 (m, 1H), 1.77
(s, 3H). 13C NMR (CDC3, 100 MHz) δ (ppm): 175.8, 175.6,
175.5, 175.2, 174.4, 174.3, 162.6, 161.9, 139.0, 137.3, 132.6,
132.5, 131.9, 131.1, 131.0, 130.3, 130.2, 129.2, 129.0, 128.5,
128.2, 127.0, 126.7, 120.5, 120.3, 60.2, 59.0, 45.4, 44.8, 31.9,
31.1, 28.8, 28.3, 19.1, 18.9, 16.0, 15.6, 9.5, 9.4. HRMS (ESI):
calcd. for [M+H]+ (C23H24N3O3) requires 390.1812 found
390.1801. HPLC (Chiralpak IB, n-hexane: i-PrOH = 90 : 10, λ =
254 nm, 1.0 mL min−1): 24.3, 38.1 min.
n-hexane: i-PrOH = 85 : 15, λ = 254 nm, 1.0 mL min−1): tR
=
44.4, 63.7 min.
1
3f: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.86
(d, J = 7.8 Hz, 2H), 7.42–7.36 (m, 2H), 7.22–7.18 (m, 2H),
7.04, (d, J = 8.1 Hz, 2H), , 3.34 (dd, J = 5.5 Hz, J′ = 9.4 Hz,
1H), 3.22–3.12 (m, 1H), 2.93 (dd, J = 9.4 Hz, J′ = 18.1 Hz, 1H),
2.33 (s, 3H), 2.18 (s, 3H), 2.12–2.08 (m, 2H), 0.81 (t, J = 7.5
Hz, 3H). 13C NMR (CDC3, 100 MHz) δ (ppm): 176.0, 175.4,
174.4, 162.0, 140.3, 138.8, 131.3, 131.2, 130.3, 127.9, 127.5,
127.5, 126.9, 120.5, 60.0, 44.7, 31.6, 28.2, 22.6, 15.9, 9.5.
HRMS (ESI): calcd. for [M+H]+ (C23H24N3O3) requires
390.1812 found 390.1817. HPLC (Chiralpak IA, n-hexane:
i-PrOH = 80 : 20, λ = 254 nm, 1.0 mL min−1): tR = 14.0,
19.5 min.
1
3l: White scum (mixture of diastereomers). H NMR (CDCl3,
400 MHz) δ (ppm): 7.90–7.85 (m, 4H), 7.42–7.35, (m, 4H),
7.25–7.00 (m, 8H), 3.62 (dd, J = 5.6 Hz, J′ = 18.5 Hz, 1H),
3.50–3.30 (m, 3H), 3.07–2.90 (m, 3H), 2.64 (dd, J = 6.5 Hz,
J′ = 18.5 Hz, 1H), 2.50–2.40 (m, 1H), 2.24 (s, 3H), 2.20 (s, 3H),
2.19 (s, 3H), 2.08 (s, 3H), 2.06 (s, 3H), 2.00–1.85 (m, 1H), 1.84
(s, 3H). 13C NMR (CDC3, 100 MHz) δ (ppm): 175.4, 175.3,
175.1, 174.7, 174.5 174.3, 162.6, 160.2, 139.0, 137.6, 137.4,
136.7, 136.7, 131.3, 131.2, 130.9, 130.4, 130.2, 130.2, 130.0,
129.9, 129.9, 129.7, 126.9, 126.7, 120.5, 120.3, 61.2, 58.9,
45.4, 44.9, 32.7, 31.1, 28.9, 27.3, 22.0, 19.4, 19.2, 19.1, 19.0,
16.4, 15.6, 9.6, 9.4. HRMS (ESI): calcd. for [M+H]+
(C25H28N3O3) requires 418.2125 found 418.2121. HPLC (Chir-
alpak IB, n-hexane: i-PrOH = 90 : 10, λ = 254 nm, 1.0 mL
min−1): 16.8, 21.6 min.
3g: White scum (mixture of diastereomers). 1H NMR (CDCl3,
400 MHz) δ (ppm): 7.90–7.80 (m, 4H), 7.45–7.10, (m, 2H),
7.00–6.95 (m, 2H), 3.40–3.30 (m, 1H), 3.25–3.20 (m, 1H),
2.90–2.75 (m, 2H), 2.00 (s, 3H), 2.00–1.95 (m, 1H), 1.95 (s,
3H), 1.92–1.70 (m, 2H), 0.80–0.75 (m, 6H). 13C NMR (CDC3,
100 MHz) δ (ppm): 176.2, 176.0, 175.4, 174.5, 174.3, 162.4,
160.3, 139.0, 138.6, 130.3,1130.3, 130.2, 130.0, 129.9, 129.9,
129.7, 129.6, 129.4, 129.3, 129.0, 126.9, 126.0, 61.4, 60.4,
60.0, 59.6, 44.5, 44.1, 32.4, 31.1, 28.5, 27.3, 16.1 15.6, 9.6, 9.5.
HRMS (ESI): calcd. for [M+H]+ (C23H24N3O3) requires
390.1812 found 390.1807. HPLC (Chiralpak IB, n-hexane:
i-PrOH = 85 : 15, λ = 254 nm, 1.0 mL min−1): tR = 14.0.5, 17.0,
21.4, 28.4 min.
1
3m: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.83
(d, J = 7.6 Hz, 2H), 7.45–7.35 (m, 5H), 7.25–7.15 (m, 3H), 3.35
(dd, J = 5.8 Hz, J′ = 9.7 Hz, 1H), 3.23–3.18 (m, 1H), 2.96 (dd, J
= 9.7 Hz, J′ = 18.1 Hz, 1H), 2.23 (s, 3H), 1.56 (s, 3H). 13C
NMR (CDC3, 100 MHz) δ (ppm): 175.6, 174.8, 174.7, 163.0,
138.6, 132.4, 130.2, 130.0, 129.9, 127.3, 126.5, 120.0, 54.4,
44.5, 31.3, 20.7, 15.3. HRMS (ESI): calcd. for [M+H]+
(C21H20N3O3) requires 362.1499, found 362.1489. HPLC (Chir-
alpak IB, n-hexane: i-PrOH = 80 : 20, λ = 254 nm, 1.0 mL
min−1): tR = 16.9, 19.3 min.
3h: White scum (mixture of diastereomers). 1H NMR (CDCl3,
400 MHz) δ (ppm): 7.90–7.80 (m, 4H), 7.44–7.16, (m, 22H),
7.13–7.06 (m, 2H), 7.01–6.94 (m, 2H), 6.54 (s, 1H), 6.47 (s,
1H), 3.42–3.10 (m, 3H), 2.87–2.76 (m, 2H), 2.42–2.35 (m, 1H),
2.04 (s, 3H), 1.95 (s, 3H), 3.25–3.20 (m, 1H), 2.90–2.75 (m,
2H), 2.00 (s, 3H), 2.10–1.90 (m, 4H), 2.00–1.95 (m, 1H), 1.95
(s, 3H), 0.77 (m, 6H). 13C NMR (CDC3, 100 MHz) δ (ppm):
176.2, 176.0, 175.4, 174.6, 174.3, 162.4, 160.3, 138.7, 138.6,
138.2, 130.4, 130.3, 130.0, 129.9, 129.8, 129.7, 129.7, 129.6,
129.4, 129.2, 129.0, 126.9, 126.8, 120.5, 120.2, 61.4, 60.4,
60.0, 59.6, 44.5, 44.1, 32.4, 31.1, 28.5, 27.3, 16.1, 15.7, 9.6,
9.5. HRMS (ESI): calcd. for [M+H]+ (C23H24N3O3) requires
1
3n: White scum. H NMR (CDCl3, 400 MHz) δ (ppm): 7.86
(d, J = 8.7 Hz, 2H), 7.42–7.36 (m, 2H), 7.22–7.17 (m, 1H), 7.01
(d, J = 8.9 Hz, 2H), 6.69 (d, J = 8.9 Hz, 2H), 3.31 (dd, J = 5.7
Hz, J′ = 9.2 Hz, 1H), 3.08–2.08 (m, 2H), 2.94 (s, 6H), 2.20 (s,
3H),1.61 (s, 3H). 13C NMR (CDC3, 100 MHz) δ (ppm): 176.5,
175.8, 175.2, 163.3, 152.0, 139.0, 130.3, 128.7, 128.3, 126.7,
1650 | Org. Biomol. Chem., 2012, 10, 1645–1652
This journal is © The Royal Society of Chemistry 2012