6.9 Hz, 1H), 6.27 (dt, J = 15.4, 1.2 Hz, 1H), 6.81 – 6.87 (m, 4H), 7.21 – 7.26 (m, 4H) ppm. 13C NMR
(126 MHz, MeOD) δ 25.85, 29.37, 46.35, 54.69, 55.76, 58.02, 61.78, 79.41, 114.14, 114.22, 126.39,
129.40, 129.45, 140.04, 140.06, 142.21, 159.92, 159.93, 182.75 ppm. HRMS (ESI): [M+H]+ calcd. for
C24H30NO5, 412.2118; found 412.2120.
4.3.9. (E)-1-[4,4-Bis(4-methoxyphenyl)but-2-en-1-yl]piperidine-3-carboxylic acid, (rac-2h)
According to GP2: Ester rac-7h (43 mg, 0.10 mmol) with NaOH (0.5 mmol, 12 M in H2O) was
hydrolyzed to get the pure product. White solid (36 mg, 91%).
IR (KBr): ṽ = 3421, 2997, 2935, 2834, 1710, 1608, 1583, 1509, 1463, 1440, 1389, 1301, 1247,
1
1175, 1110, 1032, 979, 855, 829, 772, 725, 663, 627, 580, 556 cm-1. H NMR (400 MHz, MeOD) δ
1.33 (qd, J = 12.6, 3.9 Hz, 1H), 1.55 (qt, J = 12.9, 3.8 Hz, 1H), 1.63 – 1.75 (m, 1H), 1.89 (td, J = 11.9,
2.9 Hz, 1H), 1.97 (d, J = 8.8 Hz, 1H), 2.02 (t, J = 11.4 Hz, 1H), 2.37 (tt, J = 11.8, 3.7 Hz, 1H), 2.86 (d, J
= 11.4 Hz, 1H), 3.05 (d, J = 6.9 Hz, 2H), 3.12 (d, J = 11.6 Hz, 1H), 3.76 (s, 6H), 4.64 (d, J = 7.4 Hz,
1H), 5.45 (dtd, J = 15.1, 6.9, 1.2 Hz, 1H), 6.09 (dd, J = 15.3, 7.2 Hz, 1H), 6.79 – 6.87 (m, 4H), 7.03 –
7.10 (m, 4H) ppm. 13C NMR (101 MHz, MeOD) δ 25.85, 29.41, 46.41, 53.49, 54.64, 55.75, 58.02,
62.06, 114.77, 128.01, 130.42, 137.42, 137.47, 139.27, 159.49, 182.78 ppm. HRMS (ESI): [M+H]+
calcd. for C24H30O4N, 396.2169; found: 396.2170.
4.3.10. (E)-1-[4,4,5-Tris(4-methoxyphenyl)pent-2-en-1-yl]piperidine-3-carboxylic acid, (rac-2i)
According to GP2: Ester rac-7i (75 mg, 0.14 mmol) with NaOH (0.7 mmol, 12 M in H2O) was
hydrolyzed to get the pure product. White solid (66 mg, 95%).
IR (KBr): ṽ = 3434, 2997, 2933, 2833, 1713, 1609, 1581, 1510, 1463, 1299, 1248, 1179, 1110,
1033, 829, 778, 732, 590, 546, 505 cm-1. 1H NMR (400 MHz, MeOD) δ 1.32 (qd, J = 12.8, 4.0 Hz, 1H),
1.52 (qt, J = 12.7, 3.5 Hz, 1H), 1.62 – 1.73 (m, 1H), 1.86 (td, J = 11.9, 2.8 Hz, 1H), 1.92 – 2.04 (m,
2H), 2.34 (tt, J = 11.8, 3.7 Hz, 1H), 2.80 (d, J = 11.4 Hz, 1H), 3.01 (d, J = 6.8 Hz, 2H), 3.09 (d, J = 10.9
Hz, 1H), 3.45 (s, 2H), 3.70 (s, 3H), 3.77 (s, 6H), 5.03 (dt, J = 15.6, 6.9 Hz, 1H), 6.14 (d, J = 15.7 Hz,
1H), 6.57 – 6.67 (m, 4H), 6.77 – 6.85 (m, 4H), 7.01 – 7.10 (m, 4H) ppm. 13C NMR (101 MHz, MeOD) δ
25.82, 29.41, 46.36, 47.62, 54.08, 54.68, 55.61, 55.73, 58.04, 62.46, 113.79, 114.07, 114.08, 127.70,
131.05, 131.13, 133.02, 140.26, 142.99, 159.23, 159.42, 182.77 ppm. HRMS (ESI): [M+H]+ calcd. for
C32H38NO5, 516.2744; found: 516.2752.
4.3.11. (E)-1-[4,4-Bis(4-methoxyphenyl)-5-phenylpent-2-en-1-yl]piperidine-3-carboxylic acid, (rac-2j)
According to GP2: Ester rac-7j (42 mg, 0.080 mmol) with NaOH (0.4 mmol, 12 M in H2O) was
hydrolyzed to get the pure product. White solid (36 mg, 93%).
IR (KBr): ṽ = 3420, 3030, 3000, 2934, 2863, 2835, 1711, 1607, 1581, 1509, 1454, 1384, 1345,
1289, 1250, 1180, 1151, 1120, 1033, 1002, 958, 830, 809, 756, 739, 702, 640, 601, 575 cm-1. 1H NMR
(400 MHz, MeOD) δ 1.32 (qd, J = 12.8, 4.3 Hz, 1H), 1.52 (qt, J = 13.0, 3.8 Hz, 1H), 1.63 – 1.72 (m,
1H), 1.85 (td, J = 11.9, 2.9 Hz, 1H), 1.98 (t, J = 11.5 Hz, 2H), 2.34 (tt, J = 11.8, 3.7 Hz, 1H), 2.80 (d, J
= 11.4 Hz, 1H), 3.01 (d, J = 6.9 Hz, 2H), 3.09 (d, J = 11.2 Hz, 1H), 3.52 (s, 2H), 3.78 (s, 6H), 5.04 (dt,
J = 15.6, 6.9 Hz, 1H), 6.14 (d, J = 15.6 Hz, 1H), 6.69 – 6.77 (m, 2H), 6.79 – 6.84 (m, 4H), 7.01 – 7.10
(m, 7H) ppm. 13C NMR (101 MHz, MeOD) δ 25.84, 29.42, 46.39, 48.50, 54.04, 54.71, 55.70, 58.07,
62.45, 114.08, 127.04, 127.87, 128.35, 131.12, 132.15, 139.13, 140.17, 142.79, 159.29, 182.72 ppm.
HRMS (ESI): [M+H]+ calcd. for C31H36O4N, 486.2638; found 486.2639.
4.3.12. (E)-1-(4,4,4-Triphenylbut-2-en-1-yl)piperidine-3-carboxylic acid, (rac-2k)
According to GP2: Ester rac-7k (22 mg, 0.050 mmol) with NaOH (0.25 mmol, 12 M in H2O) was
hydrolyzed to get the pure product. White solid (20 mg, 97%).
IR (KBr): ṽ = 3083, 3060, 3030, 2924, 2854, 2793, 2760, 2739, 1952, 1679, 1582, 1491, 1464,
1443, 1397, 1365, 1345, 1305, 1365, 1345, 1305, 1269, 1241, 1203, 1180, 1147, 1138, 1116, 1090,
1
1031, 1001, 990, 974, 957, 936, 908, 787, 772, 755, 739, 711, 700, 668, 654 cm- 1. H NMR (400
MHz, MeOD) δ 1.41 – 1.55 (m, 1H), 1.53 – 1.69 (m, 1H), 1.70 – 1.82 (m, 1H), 1.95 (d, J = 12.9 Hz,
23