3-1 分析儀器及基本實驗操作
1. 所有反應物和溶劑均為試藥級或分析級，純化方式依 Perrin, D. D.; Armarego, W. L. F.及 Perrin, D. R.所著 Purification of Laboratory Chemicals, 7th ed., Butterworth-Heinemann, 2013 的方法處理。四氫呋喃、二氯甲烷、甲苯、乙腈 經過溶劑純化系統乾燥及純化(active alumina column)。
2. 分析用之薄層色層分析片(Thin Layer Chromatography，簡稱 TLC)：使用 Silica gel 60 F254 Merck 之玻璃 TLC 薄片，展開後以紫外燈(254 nm)檢視。
3. 管柱色層分析(Column Chromatography)：使用 Merck Silica gel F60，230-400 mesh ATSM 為填充物，用加壓快速層析(flash column chromatography)依 Still 的操作方法來分離。沖堤液(eluent)若是兩種溶劑系統，是以體積比值而配 置，記錄方法為兩種溶液之體積比值。(J. Org. Chem. 1978, 43, 2923.)
4. 減壓式迴旋濃縮儀：使用 Büchi Rotavapor R-114 型旋轉濃縮器，連接空氣式 或水流式幫浦。
5. 核磁共振光譜儀(NMR)：以 Bruker Avance 型(400 MHz)核磁共振光譜儀作為 測定儀器，樣品之溶劑為氘化氯仿(CDCl3)。化學位移(δ, chemical shift)以 ppm 為單位，1H-NMR 光譜化學位移以四甲基矽烷(tetramethylsilane，簡稱 TMS)
6. 紅外線光譜儀(IR Spectroscopy)：使用 Perkin Elmer FTIR 型紅外線光譜儀為測 定儀器。
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7. 質譜(Mass Spectroscopy，簡稱 MS)：使用 Finnigan TSQ-700 型質譜儀作為 測定儀器。係委託國科會台灣師範大學貴重儀器中心代為測定。高解析質譜 (High Resolution Mass Spectroscopy，簡稱 HRMS)：委託中研院儀器服務中心 (EI、ESI 和 FAB)代為測定。
8. X-ray 單晶繞射：使用 Nonius Kappa CCD Axia 四環單晶繞射儀、
Enraf-Nonius FR-590 四環單晶繞射儀(CAD4)作為測定儀器。由國科會 台灣師範大學貴重儀器中心代為測定。
9. 高效能液相層析儀(HPLC)：使用 JASCO 880-PU 型高壓幫浦及 JASCO 870-UV 型紫外／可見光檢測器；管柱選用 Chiralpak AD-H、OD-H。
10. 旋光儀：使用 JASCO Co. DIP-1000 型 Digital polarimeter 自動旋光度計。
11. 熔點：使用 MEL-TEMP II 型做測定熔點儀器。
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3-2-2 動力學光學分割去對稱反應一般實驗步驟
將外消旋硝基烯丙醇97a、3-苯基戊二酸酐102與雙官能基硫尿素-辛可尼汀 衍生催化劑107置於反應瓶中(含磁石攪拌子)，加入甲苯於室溫反應4-48小時。以 TLC與1H NMR偵測反應，待反應轉化率約50%時加水中止反應，以二氯甲烷萃 取，收集有機層，再以飽和食鹽水洗之，取有機層，加入無水硫酸鎂除水，過濾、
減壓濃縮至乾，以管柱層析純化，沖提液為正己烷：乙酸乙酯=2：1，得到淡黃 色油狀產物。
Ethyl 2-hydroxy-3-nitro-4-phenylbut-3(E)-enoate (97a)
反應時間：4小時；產率：50%，鏡像超越值：97% ee
1H NMR (400 MHz, CDCl3): δ 8.33 (s, 1H), 7.58-7.56 (m, 2H), 7.51-7.49 (m, 3H), 5.24 (d, J = 6.0 Hz, 1H), 4.37-4.22 (m, 2H), 3.68 (d, J = 6.0 Hz, 1H), 1.27 (t, J = 7.2 Hz, 3H);
13C NMR (100 MHz, CDCl3): δ 1171.2, 148.5, 139.9, 131.7, 131.6, 130.5, 129.9, 66.6, 63.7, 14.6 ppm; FTIR (ν/cm-1): 3491, 3070, 2982, 1749, 1650, 1532, 1447, 1336, 1296, 1255, 1222, 1104, 1012; HRMS (ESI) m/z calcd. for C12H13NO5Na [M+Na]+ 274.0691, found 274.0685; HPLC [Chiralcel OD-H, i-Propanol/Hexanes = 10/90, 0.5 mL/min, = 254 nm, retention time：18.3 min (minor), 22.6 min (major)].
40
Ethyl 2-hydroxy-4-(4-methylphenyl)-3-nitrobut-3(E)-enoate (97b)
反應時間：4小時；產率：44%，鏡像超越值：86% ee
1H NMR (400 MHz, CDCl3): δ 8.31 (s, 1H), 7.47 (d, J = 8 Hz, 2H), 7.30 (d, J = 8 Hz, 2H), 5.25 (d, J = 6.0 Hz, 1H), 4.36-4.22 (m, 2H), 3.65 (d, J = 6.0 Hz, 1H), 2.42 (s, 3H), 1.26 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.6, 147.1, 141.9, 139.5, 130.0, 128.0, 66.0, 62.9, 21.5, 13.9 ppm; FTIR (ν/cm-1): 3491, 2982, 2915, 2849, 1749, 1650, 1609, 1524, 1329, 1292, 1259, 1229, 1185, 1104, 1071, 1019; HRMS (EI) m/z calcd.
for C13H15NO5 [M]+ 265.0950, found 265.0955; HPLC [Chiralcel OD-H, i-Propanol/
Hexanes = 5/95, 1.0 mL/min, = 254 nm, retention time：13.5 min (minor), 16.1 min (major)].
Ethyl 4-(4-chlorophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate (97c)
反應時間：4小時；產率：49%，鏡像超越值：96% ee
1H NMR (400 MHz, CDCl3): δ 8.27 (s, 1H), 7.53-7.46 (m, 4H), 5.15 (d, J = 6.0 Hz, 1H), 4.37-4.22 (m, 2H), 3.67 (d, J = 6.0 Hz, 1H), 1.27 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.2, 148.1, 137.9, 137.5, 131.1, 129.6, 129.2, 65.8, 63.1, 14.0 ppm; FTIR
41
(ν/cm-1): 3454, 2989, 2923, 2841, 1749, 1653, 1591, 1528, 1491, 1340, 1255, 1229, 1093, 1012; HRMS (EI) m/z calcd. for C12H12ClNO5 [M]+ 285.0404, found 285.0410;
HPLC [Chiralcel OD-H, i-Propanol/ Hexanes = 5/95, 0.5 mL/min,
= 254 nm,
retention time：33.0 min (minor), 38.6 min (major)].
Ethyl 4-(2-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate (97d)
反應時間：4小時；產率：49%，鏡像超越值：78% ee
1H NMR (500 MHz, CDCl3): δ 8.37 (s, 1H), 7.70 (d, J = 6.4 Hz, 1H), 7.58 (d, J = 6.0 Hz, 1H), 7.43 (dd, J = 6.0 Hz, 1H), 7.36 (dd, J = 6.4, 6.0 Hz, 1H), 5.07 (d, J = 4.4 Hz, 1H), 4.36-4.24 (m, 2H), 3.63 (d, J = 4.8 Hz, 1H), 1.29 (t, J = 5.6 Hz, 3H); 13C NMR (125 MHz, CDCl3): δ 170.2, 148.7, 138.2, 133.3, 132.0, 131.8, 130.5, 127.9, 124.9, 65.9, 63.1, 13.9 ppm; FTIR (ν/cm-1): 3469, 2989, 2915, 2849, 1749, 1653, 1532, 1465, 1436, 1347, 1263, 1229, 1104, 1027; HRMS (ESI) m/z calcd. for C12H12BrNO5Na [M+Na]+ 351.9797, found 351.9794; HPLC [Chiralcel OD-H, i-Propanol/Hexanes = 3/97, 0.7 mL/min, = 254 nm, retention time：22.2 min (minor), 24.6 min (major)].
42
Ethyl 4-(3-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate (97e)
反應時間：4小時；產率：53%，鏡像超越值：94% ee
1H NMR (400 MHz, CDCl3): δ 8.23 (s, 1H), 7.72 (s, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.50 (d, J = 7.6 Hz, 1H), 7.37 (dd, J = 8.0, 7.6 Hz, 1H), 5.16 (d, J = 6.0 Hz, 1H), 4.38-4.26 (m, 2H), 3.67 (d, J = 6.0 Hz, 1H), 1.29 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.1, 148.7, 137.2, 133.9, 132.8, 132.4, 130.7, 128.1, 123.2, 65.7, 63.1, 14.0 ppm; FTIR (ν/cm-1): 3454, 2989, 2915, 2849, 1749, 1650, 1561, 1528, 1473, 1340, 1259, 1229, 1108, 1071, 1016; HRMS (EI) m/z calcd. for C12H12BrNO5 [M]+ 328.9899, found 328.9908; HPLC [Chiralcel OD-H, i-Propanol/Hexanes = 3/97, 0.5 mL/min, = 254 nm, retention time：44.2 min (minor), 52.6 min (major)].
43
Ethyl 4-(4-bromophenyl)-2-hydroxy-3-nitrobut-3(E)-enoate (97f)
反應時間：4小時；產率：49%，鏡像超越值：80% ee
1H NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 7.63 (d, J = 6.8 Hz, 2H), 7.44 (d, J = 6.8 Hz, 2H), 5.15 (d, J = 4.8 Hz, 1H), 4.36-4.23 (m, 2H), 3.70 (d, J = 4.8 Hz, 1H), 1.27 (t, J = 5.8 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.1, 148.1, 137.9, 132.5, 131.2, 129.7, 125.9, 65.8, 63.1, 13.9 ppm; FTIR (ν/cm-1): 3476, 2989, 2915, 2849, 1749, 1650, 1587, 1532, 1488, 1403, 1336, 1303, 1259, 1233, 1100, 1071, 1012; HRMS (EI) m/z calcd. for C12H12BrNO5 [M]+ 328.9899, found 328.9896; HPLC [Chiralcel OD-H, i-Propanol/Hexanes = 10/90, 0.8 mL/min,
= 254 nm, retention time：14.8 min
(minor), 20.3 min (major)].44
Ethyl 2-hydroxy-3-nitro-4-(thiophen-2-yl)but-3(E)-enoate (97g)
反應時間：4小時；產率：37%，鏡像超越值：74% ee
1H NMR (400 MHz, CDCl3): δ 8.38 (s, 1H), 7.72 (d, J = 4.0 Hz, 1H), 7.56 (d, J = 3.2 Hz, 1H), 7.22 (dd, J = 4.0, 4.0 Hz, 1H), 5.58 (d, J = 4.8 Hz, 1H), 4.36-4.24 (m, 2H), 3.73 (d, J = 5.2 Hz, 1H), 1.26 (t, J = 5.8 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 170.2, 144.6, 136.1, 133.4, 132.8, 131.8, 128.7, 66.1, 62.9, 13.9 ppm; FTIR (ν/cm-1): 3432, 2989, 2915, 2841, 1749, 1635, 1521, 1418, 1307, 1252, 1218, 1159, 1100, 1053, 1016;
HRMS (EI) m/z calcd. for C10H11NO5S [M]+ 257.0358, found 257.0362; HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 10/90, 1.0 mL/min,
= 254 nm, retention
time：33.0 min (minor), 39.9 min (major)].45
5-(((E)-1-ethoxy-3-nitro-1-oxo-4-phenylbut-3-en-2-yl)oxy)-5-oxo-3-phenyl pentanoic acid (109a)
反應時間：4 小時；產率：37%，鏡像超越值：90% ee
1H NMR (400 MHz, CDCl3): δ 8.35 (s, 1H), 7.49-7.40 (m, 3H), 7.29-7.23 (m, 4H), 7.21-7.15 (m, 3H), 6.47 (s, 1H), 4.15 (q, J = 7.2 Hz, 2H), 3.70-3.62 (m, 1H), 2.97-2.66 (m, 4H), 1.17 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 176.7, 169.6, 165.7, 144.6, 141.7, 140.6, 131.3, 130.2, 129.6, 129.2, 128.7, 128.6, 127.2, 127.2, 127.1, 65.5, 62.6, 40.1, 39.8, 37.6, 13.8 ppm; FTIR (ν/cm-1): 3061, 3023, 2977, 2924, 1745, 1730, 1649, 1531, 1337, 1295, 1219, 1139, 1051; HRMS (ESI) m/z calcd. for C23H23NO8Na [M+Na]+ 464.1321, found 464.1317;
HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 20/80, 0.2 mL/min,
= 254 nm,
retention time：69.0 min (major), 88.0 min (minor)]; []D31= -48.27o (c=1, CH2Cl2)
46
5-(((E)-1-ethoxy-3-nitro-1-oxo-4-(p-tolyl)but-3-en-2-yl)oxy)-5-oxo-3-phenyl pentanoic acid (109b)
反應時間：4 小時；產率：47%，鏡像超越值：83% ee
1H NMR (400 MHz, CDCl3): δ 8.32 (s, 1H), 7.27-7.25 (m, 2H), 7.23-7.20 (m, 5H), 7.19-7.17 (m, 2H), 6.50 (s, 1H), 4.18-4.12 (m, 2H), 3.70-3.62 (m, 1H), 2.96-2.66 (m, 4H), 2.39 (s, 3H), 1.16 (t, J = 1.16 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 176.0, 169.7, 165.8, 143.9, 142.3, 141.8, 140.8, 130.0, 129.9, 128.7, 128.6, 127.4, 127.3, 127.2, 127.1, 65.7, 62.6, 40.0, 39.9, 37.7, 21.5, 13.8 ppm; FTIR (ν/cm-1): 3031, 2977, 2924, 2855, 1764, 1741, 1710, 1649, 1527, 1367, 1333, 1295, 1223, 1139, 1051; HRMS (ESI) m/z calcd. for C24H25NO8Na [M+Na]+ 478.1478, found 478.1476; HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 22/78, 0.2 mL/min,
= 254 nm, retention time：45.6 min
(major), 49.1 min (minor)]; []D31= -28.90o (c=1, CH2Cl2)
47
5-(((E)-4-(4-chlorophenyl)-1-ethoxy-3-nitro-1-oxobut-3-en-2-yl)oxy)-5-oxo-3- phenylpentanoic acid (109c)
反應時間：4 小時；產率：46%，鏡像超越值：71% ee
1H NMR (400 MHz, CDCl3): δ 8.27 (s, 1H), 7.38 (d, J
= 8.4 Hz, 2H), 7.28-7.24 (m, 3H), 7.21-7.18 (m, 4H), 6.40 (s, 1H), 4.19-4.13 (m, 2H), 3.67-3.63 (m, 1H), 2.97-2.66 (m, 4H), 1.17 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 175.8, 169.6, 165.6, 145.0, 141.7, 139.1, 137.8, 130.9, 129.6, 128.7, 128.6, 127.3, 127.2, 65.3, 62.7, 40.0, 39.8, 37.7, 13.8 ppm; FTIR (ν/cm-1): 2985, 2924, 2847, 1768, 1745, 1714, 1653, 1528, 1333, 1229, 1139, 1051; HRMS (ESI) m/z calcd. for C23H22ClNO8Na [M+Na]+ 498.0932, found 498.0936; HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 25/75, 0.2 mL/min,
= 254 nm, retention time：49.1 min (major), 52.3 min (minor)]; []D31
= -36.39o (c=1, CH2Cl2)
48
5-(((E)-4-(2-bromophenyl)-1-ethoxy-3-nitro-1-oxobut-3-en-2-yl)oxy)-5-oxo-3- phenylpentanoic acid (109d)
反應時間：4 小時；產率：32%，鏡像超越值：78% ee
1H NMR (400 MHz, CDCl3): δ 8.37 (s, 1H), 7.66-7.64 (m, 1H), 7.31-7.25 (m, 4H), 7.23-7.18 (m, 3H), 7.06-7.03 (m, 1H), 6.26 (s, 1H), 4.17-4.10 (m, 2H), 3.67-3.60 (m, 1H), 2.94-2.63 (m, 4H), 1,18 (t, J = 7.12 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 176.6, 169.4, 165.5, 145.8, 141.7, 139.7, 133.2, 132.1, 131.3, 130.1, 128.7, 128.6, 127.9, 127.2, 127.2, 127.2, 65.3, 62.7, 40.0, 39.8, 37.6, 13.8 ppm; FTIR (ν/cm-1): 2916, 1744, 1729, 1710, 1535, 1340, 1280, 1223, 1140, 1024; HRMS (EI) m/z calcd. for C23H23BrNO8
[M+H]+ 520.0607, found 520.0602; HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 25/75, 0.2 mL/min, = 254 nm, retention time：42.3 min (major), 61.7 min (minor)];
[]D31
= -10.68o (c=1, CH2Cl2)
49
5-(((E)-4-(3-bromophenyl)-1-ethoxy-3-nitro-1-oxobut-3-en-2-yl)oxy)-5-oxo-3-phe nylpentanoic acid (109e)
反應時間：4 小時；產率：43%，鏡像超越值：84% ee
1H NMR (400 MHz, CDCl3): δ 8.23(s, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.46 (s, 1H), 7.29-7.28 (m, 2H), 7.25-7.23 (m, 2H), 7.21-7.17 (m, 3H), 6.38 (s, 1H), 4.17 (q, J = 7.14 Hz, 2H), 3.68-3.61 (m, 1H), 2.98-2.64 (m, 4H), 1.19 (t, J = 7.12 Hz, 3H); 13C NMR (100 MHz, CDCl3):
δ 175.7, 169.5, 165.5, 145.7, 141.7, 138.6, 134.1, 132.3, 132.2, 130.7, 128.7, 128.6,
127.7, 127.3, 127.2, 127.2, 123.2, 65.2, 62.8, 40.0, 39.8, 37.7, 13.9 ppm; FTIR (ν/cm-1): 2985, 2924, 2855, 1741, 1730, 1710, 1539, 1531, 1337, 1227, 1143, 1055;
HRMS (ESI) m/z calcd. for C23H22BrNO8Na [M+Na]+ 542.0426, found 542.0428;
HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 25/75, 0.2 mL/min,
= 254 nm,
retention time：51.8 min (major), 72.3 min (minor)]; []D31= -6.58o (c=1, CH2Cl2)
50
5-(((E)-4-(4-bromophenyl)-1-ethoxy-3-nitro-1-oxobut-3-en-2-yl)oxy)-5-oxo-3-phe nylpentanoic acid (109f)
反應時間：4 小時；產率：38%，鏡像超越值：56% ee
1H NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 7.53 (d, J
= 8.4 Hz, 2H), 7.25-7.22 (m, 2H), 7.19-7.17 (m, 3H), 7.12 (d, J = 8.4 Hz, 2H), 6.39 (s, 1H), 4.18-4.13 (m, 2H), 3.67-3.60 (m, 1H), 2.96-2.64 (m, 4H), 1.16 (t, J = 7.14 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 177.1, 169.6, 165.5, 144.9, 141.6, 139.2, 132.5, 130.9, 130.9, 129.0, 128.6, 128.6, 127.2, 127.1, 126.0, 65.2, 62.7, 40.1, 39.7, 37.5, 13.8 ppm; FTIR (ν/cm-1): 2977, 2916, 1730, 1710, 1535, 1371, 1280, 1215, 1070; HRMS (ESI) m/z calcd. for C23H22BrNO8Na [M+Na]+ 542.0426, found 542.0425; HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 10/90, 0.5 mL/min, = 254 nm, retention time：53.1 min (major), 59.3 min (minor)];
[]D31
= -3.35o (c=1, CH2Cl2)
51
5-(((S,E)-1-ethoxy-3-nitro-1-oxo-4-(thiophen-2-yl)but-3-en-2-yl)oxy)-5-oxo-3-phe nylpentanoic acid (109g)
反應時間：4 小時；產率：39%，鏡像超越值：92% ee
1H NMR (400 MHz, CDCl3): δ 8.43 (s, 1H), 7.69 (d, J
= 5.0 Hz, 1H), 7.47 (d, J = 3.7 Hz, 1H), 7.26-7.22 (m, 1H), 7.21-7.19 (m, 4H), 7.18-7.16 (m, 1H), 6.72 (s, 1H), 4.23-4.15 (m, 2H), 3.70-3.62 (m, 1H), 2.96-2.63 (m, 4H), 1.18 (t, J = 7.14 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 176.7, 170.1, 165.4, 141.7, 140.8, 136.8, 134.4, 133.1, 132.5, 128.8, 128.6, 128.5, 127.2, 127.1, 127.0, 65.7, 62.6, 40.0, 39.9, 37.6, 13.8 ppm; FTIR (ν/cm-1):
3107, 2977, 2924, 1764, 1737, 1710, 1634, 1524, 1333, 1310, 1215, 1139, 1051;
HRMS (ESI) m/z calcd. for C21H21NO8SNa [M+Na]+ 470.0886, found 470.0884;
HPLC [Chiralcel AD-H, i-Propanol/Hexanes = 22/78, 0.2 mL/min,
= 254 nm,
retention time：53.1 min (major), 59.3 min (minor)]; []D31 = +119.64o (c=1, CH2Cl2)52
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