– 2.50 (m, 2H), 2.22 – 2.15 (m, 1H), 2.14 – 2.04 (m, 2H), 1.22 (d, J
= 7.0 Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ 214.55 ,
195.44 , 170.37 , 150.48 , 140.73 , 129.11 , 123.88 , 61.86 , 57.52 ,
43.68 , 37.62 , 33.39 , 19.83 , 13.99 . IR (thin film, cm-1) 2979,
2917, 1752, 1723, 1695, 1603, 1526, 1346, 1215, 1109, 992, 854,
747, 687. HRMS (ESI) calcd for C16H17NO6Na+: 342.0948, found
342.0947.
61.66 , 61.44 , 43.92 , 41.74 , 33.07 , 30.38 , 26.16 , 24.85 , 13.98 .
IR data was reported previously.[17] HRMS (ESI) calcd for
C
18H22O4Na+: 325.1410, found 325.1410.
4p: 80% yield, 97% ee. [α]D = 97.8 (c = 1.50, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 10:90, flow
rate = 1.0 mL/min, λ = 254 nm, retention time: 69.95 min (major),
66.57 min (minor). 1H NMR (400 MHz, Chloroform-d) δ 8.28 (d, J =
8.8 Hz, 2H), 8.08 (d, J = 8.9 Hz, 2H), 4.26 (dd, J = 7.1, 4.3 Hz, 2H),
3.50 (d, J = 17.2 Hz, 1H), 3.30 (d, J = 17.2 Hz, 1H), 2.98 - 2.84 (m,
1H), 2.55 - 2.44 (m, 2H), 2.15 - 1.97 (m, 1H), 1.79 (d, J = 2.8 Hz,
4H), 1.28 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) δ
207.25 , 195.77 , 171.79 , 150.26 , 141.48 , 129.08 , 123.78 ,
61.76 , 59.63 , 44.25 , 40.52 , 37.26 , 26.98 , 21.95 , 14.06 . IR (thin
film, cm-1) 2942, 2868, 1729, 1710, 1698, 1603, 1526, 1347, 1317,
4k: 85% yield, 96% ee. [α]D = -25.8 (c = 2.28, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 10:90, flow
rate = 1.0 mL/min, λ = 242 nm, retention time: 13.39 min (major),
15.05 min (minor). 1H NMR (400 MHz, Chloroform-d) δ 8.05 (s,
1H), 7.85 (d, J = 7.9 Hz, 1H), 7.68 (d, 1H), 7.33 (t, J = 7.9 Hz, 1H),
4.16 (q, J = 7.1 Hz, 2H), 3.79 (d, J = 18.6 Hz, 1H), 3.40 (d, J = 18.6
Hz, 1H), 2.90 - 2.40 (m, 3H), 2.23 - 1.99 (m, 3H), 1.22 (t, J = 7.2 Hz,
3H). 13C NMR (101 MHz, Chloroform-d) δ 214.75 , 195.48 , 170.51 , 1213, 1134, 1030, 854, 796, 737, 686. HRMS (ESI) calcd for
138.04 , 136.28 , 131.12 , 130.25 , 126.56 , 123.01 , 61.76 , 57.46 ,
43.42 , 37.68 , 33.40 , 19.83 , 14.01 .IR (thin film, cm-1) 2962,
2917, 1751, 1723, 1690, 1567, 1351, 1214, 1108, 1094, 1031, 995,
784, 680. HRMS (ESI) calcd for C16H17BrO4Na+: 375.0202, found
375.0200.
C
17H19O6NNa+: 356.1105, found 356.1103.
4q: 82% yield, 98% ee. [α]D = 80.8 (c = 2.35, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 5:95, flow
rate = 1.0 mL/min, λ = 233 nm, retention time: 18.93 min (major),
17.16 min (minor). 1H NMR (400 MHz, Chloroform-d) δ 8.03 (d, J =
8.1 Hz, 2H), 7.71 (d, J = 8.1 Hz, 2H), 4.25 (dd, J = 7.2, 4.0 Hz, 2H),
3.52 (d, J = 17.3 Hz, 1H), 3.32 (d, J = 17.3 Hz, 1H), 2.99 - 2.80 (m,
1H), 2.57 - 2.34 (m, 2H), 2.09 (dd, J = 6.3, 3.1 Hz, 1H), 1.79 (m, 4H),
1.27 (t, J = 7.2 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) δ
207.11 , 196.17 , 171.82 , 139.66 , 128.36 , 125.60, 126.56 , 61.63 ,
59.34 , 44.09 , 40.50 , 37.03 , 26.90 , 21.97 , 14.01 . IR data wa
reported previously.[3g] HRMS (ESI) calcd for C18H19O4F3Na+:
4l: 61% yield, 86% ee. [α]D = -23.1 (c = 0.76, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 10:90, flow
rate = 1.0 mL/min, λ = 268 nm, retention time: 32.36 min (major),
36.74 min (minor). 1H NMR (500 MHz, Chloroform-d) δ 7.91 (d, J =
8.9 Hz, 2H), 6.92 (d, J = 8.9 Hz, 2H), 4.16 (d, J = 7.1 Hz, 2H), 3.86 (s,
3H), 3.79 (d, J = 18.3 Hz, 1H), 3.44 (d, J = 18.3 Hz, 1H), 2.69 - 2.56
(m, 2H), 2.53 - 2.42 (m, 1H), 2.28 - 2.03 (m, 3H), 1.23 (t, J = 7.1 Hz,
3H). 13C NMR (126 MHz, Chloroform-d) δ 215.27 , 195.20 , 170.86 , 379.1128, found 379.1126.
163.74 , 130.34 , 129.47 , 113.77 , 61.62 , 57.51 , 55.50 , 43.20 ,
37.79 , 33.45 , 19.86 , 14.01 . IR (thin film, cm-1) 2962, 2943, 2917, analysis: Daicel Chiralpak AD-H, iso-propanol/hexane = 30:70, flow
4r: >99% yield, 77% ee. [α]D = -10.9 (c = 2.68, CHCl3). HPLC
25
1750, 1722, 1678, 1601, 1510, 1261, 1229, 1170, 1112, 1092,
1030, 988, 833, 752. HRMS (ESI) calcd for C17H20O5Na+: 327.1203,
found 327.1203.
rate = 1.0 mL/min, λ = 259 nm, retention time: 29.41 min (major),
19.32 min (minor). 1H NMR (500 MHz, Chloroform-d) δ 8.32 (d, J =
8.3 Hz, 2H), 8.12 (d, J = 8.4 Hz, 2H), 4.52 (m, 1H), 4.44 (m, 1H),
3.98 (d, J = 18.8 Hz, 1H), 3.60 (d, J = 18.8 Hz, 1H), 3.15 - 2.91 (m,
1H), 2.29 (s, 4H). 13C NMR (126 MHz, Chloroform-d) δ 200.56 ,
194.94 , 174.88 , 150.78 , 139.99 , 129.27 , 124.08 , 66.98 , 58.24 ,
44.09 , 30.72 , 25.71 . IR data was reported previously.[3g] HRMS
(APCI) calcd for C14H14O6N+: 292.0816, found 292.0812.
4m: 52% yield, 94% ee. [α]D = -26.3 (c = 1.50, CHCl3). HPLC
25
analysis: Daicel Chiralpak AD-H, iso-propanol/hexane = 10:90, flow
rate = 1.0 mL/min, λ = 235 nm, retention time: 10.01 min (major),
12.21 min (minor). 1H NMR (400 MHz, Chloroform-d) δ 8.04 (d, J =
8.1 Hz, 2H), 7.72 (d, J = 8.2 Hz, 2H), 4.17 (q, J = 7.1 Hz, 2H), 3.84 (d,
J = 18.6 Hz, 1H), 3.44 (d, J = 18.6 Hz, 1H), 2.80 - 2.64 (m, 1H), 2.60
- 2.54 (m, 2H), 2.26 - 1.99 (m, 3H), 1.23 (t, J = 7.1 Hz, 3H). 13C NMR
(101 MHz, Chloroform-d) δ 214.70 , 195.90 , 170.48 , 138.98 ,
128.39 , 125.75 , 61.79 , 57.48 , 43.57 , 37.66 , 33.41 , 19.83 ,
13.98 . IR (thin film, cm-1) 2962, 2943, 2917, 1751, 1723, 1693,
1512, 1410, 1324, 1168, 1130, 1111, 1066, 1015, 993, 833, 752.
HRMS (ESI) calcd for C17H20O5Na+: 365.0971, found 365.0970.
4n: 70% yield, 98% ee. [α]D25 = 99.0 (c = 1.10, CHCl3). HPLC
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 10:90, flow
rate = 1.0 mL/min, λ = 240 nm, retention time: 32.76 min (major),
29.17 min (minor). 1H NMR (500 MHz, Chloroform-d) δ 7.94 (d, J =
6.9 Hz, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.44 (t, J = 7.6 Hz, 2H), 4.23 (dd,
J = 7.2, 4.6 Hz, 2H), 3.56 (d, J = 17.4 Hz, 1H), 3.38 (d, J = 17.4 Hz,
1H), 2.92 - 2.74 (m, 1H), 2.59 - 2.40 (m, 2H), 2.08 (dd, J = 6.1, 3.1
Hz, 1H), 1.89 - 1.72 (m, 4H), 1.26 (t, J = 7.1 Hz, 3H). 13C NMR (126
MHz, Chloroform-d) δ 207.29 , 196.97 , 172.03 , 136.83 , 133.10 ,
128.53 , 128.05 , 61.53 , 58.93 , 44.02 , 40.55 , 36.74 , 26.83 ,
22.03 , 14.06 . IR data was reported previously.[16] HRMS (ESI)
calcd for C17H20O4Na+: 311.1254, found 311.1255.
4s: 58% yield, 94% ee. [α]D = 13.7 (c = 0.76, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 30:70, flow
rate = 1.0 mL/min, λ = 242 nm, retention time: 12.41 min (major),
10.88 min (minor). 1H NMR (500 MHz, Chloroform-d) δ 7.96 (d, J =
7.0 Hz, 2H), 7.58 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.7 Hz, 2H), 3.86 -
3.55 (q, 2H), 2.60 (m, 1H), 2.49 m, 1H), 2.21 (s, 3H), 1.55 (s, 3H),
1.06 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ
208.86 , 206.44 , 197.35 , 136.47 , 133.53 , 128.69 , 128.10 ,
64.19 , 44.89 , 31.91 , 26.52 , 19.52 , 7.99 . IR data was reported
previously.[3g] HRMS (ESI) calcd for C15H18O3Na+: 269.1148, found
269.1148.
4t: 69% yield, 95% ee. [α]D25 = 7.14 (c = 1.56, CHCl3). HPLC
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 30:70, flow
rate = 1.0 mL/min, λ = 282 nm, retention time: 30.71 min (major),
27.68 min (minor). 1H NMR (500 MHz, Chloroform-d) δ 8.03 (d, J =
8.4 Hz, 2H), 7.68 (d, J = 8.1 Hz, 2H), 7.62 (d, J = 6.9 Hz, 2H), 7.47 (t,
J = 7.5 Hz, 2H), 7.41 (t, 1H), 3.73 (q, 2H), 2.62 (dd, J = 18.3, 7.2 Hz,
1H), 2.52 (dd, J = 18.3, 7.1 Hz, 1H), 2.22 (s, 3H), 1.57 (s, 3H), 1.08
(t, J = 7.2 Hz, 3H). 13C NMR (126 MHz, Chloroform-d) δ 208.90 ,
206.48 , 196.95 , 146.22 , 139.70 , 135.17 , 128.99 , 128.73 ,
128.36 , 127.31 , 127.28 , 64.25 , 44.91 , 31.94 , 26.54 , 19.56 ,
8.02 . IR (thin film, cm-1) 2981, 2938, 2923, 2853, 1698, 1678,
1603, 1449, 1400, 1351, 1224, 1169, 958, 834, 765, 721, 691.
HRMS (ESI) calcd for C21H22O3Na+: 345.1461, found 345.1460.
4o: 66% yield, 99% ee. [α]D = 32.2 (c = 1.51, CHCl3). HPLC
25
analysis: Daicel Chiralpak OJ-H, iso-propanol/hexane = 5:95, flow
rate = 1.0 mL/min, λ = 240 nm, retention time: 32.29 min (major),
30.30 min (minor). 1H NMR (400 MHz, Chloroform-d) δ 7.95 (d, J =
6.9 Hz, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.45 (t, J = 7.5 Hz, 2H), 4.20 (q,
J = 7.1 Hz, 2H), 3.85 (d, J = 17.7 Hz, 1H), 3.28 (d, J = 17.7 Hz, 1H),
3.01 - 2.83 (m, 1H), 2.69 - 2.51 (m, 1H), 2.30 (d, J = 9.6 Hz, 1H),
2.16 (d, J = 9.5 Hz, 1H), 1.86 (s, 1H), 1.80 - 1.51 (m, 4H), 1.37 - 1.27
(m, 1H), 1.22 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, Chloroform-d)
δ 209.08 , 197.28 , 171.89 , 136.88 , 133.11 , 128.54 , 128.03 ,
This article is protected by copyright. All rights reserved.
4u: 52% yield, 97% ee. [α]D = -3.4 (c = 0.55, CHCl3). HPLC
25
analysis: Daicel Chiralpak OD-H, iso-propanol/hexane = 20:80,
flow rate = 1.0 mL/min, λ = 240 nm, retention time: 9.67 min
(major), 10.70 min (minor). 1H NMR (500 MHz, Chloroform-d) δ
7.96 (d, J = 7.0 Hz, 2H), 7.58 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.7 Hz,