Download (3249Kb) - D-Scholarship@Pitt - University of Pittsburgh

Cbz
N
MeO2C 5-Ethylidene-2-methyl-4-(2-methylpropenyl)-3-pentyl-5,6-dihydro-2H-pyridine-1,2-
111k
dicarboxylic acid-1-benzyl ester 2-methyl ester (111k). Prepared by following general
procedure G, using: 73k (33 mg, 77 µmol), [Rh(CO)2Cl]2 (2 mg, 5 µmol). Yield 111k (29 mg,
78%).
1 H NMR (300 MHz, DMSO-d6, 323 K): δ 7.45-7.38 (m, 5H), 5.61 (s, 1H), 5.52 (q, J = 7.0 Hz,
1H), 5.20-5.11 (m, 2H), 4.73 (d, J = 14.7 Hz, 1H), 3.66 (d, J = 14.7 Hz, 1H), 2.00-1.93 (m, 1H),
1.83 (s, 3H), 1.74 (d, J = 7.0 Hz, 1H), 1.57 (s, 3H), 1.48 (s, 3H), 1.34-1.23 (m, 4H), 0.86 (t, J =
6.5 Hz, 3H); 13 C NMR (75 MHz, DMSO-d6, 323 K): δ 172.2, 154.6, 137.0, 136.1, 134.0, 133.2,
131.4, 128.9, 128.4, 128.1, 121.2, 120.7, 67.2, 65.4, 52.2, 31.4, 29.0, 25.0, 23.1, 19.1, 13.9, 13.5;
IR (thin film): ν 1745, 1703, 1408, 1245 cm -1 ; MS m/z (%) 425 (20), 366 (6), 135 (95), 133
(100); EI-HRMS calcd for C26H35NO4 m/z [M] + 425.2566; found 425.2549.
Boc
MeO 2C
N
Bn
2-Benzyl-5-ethylidene-4-hept-1-enyl-3-methyl-5,6-dihydro-2H-pyridine-1,2-dicarboxylic
111l
acid 1-tert-butyl ester 2-methyl ester (111l). Prepared by following general procedure G, using:
C 5H 11
73l (45 mg, 96 µmol), [Rh(CO)2Cl]2 (3 mg, 8 µmol). Yield 111l (36 mg, 80%).
1 H NMR (300 MHz, DMSO-d6, 325 K): δ 7.21-7.15 (m, 3H), 7.02-6.93 (m, 2H), 5.82 (d, J =
16.0 Hz, 1H), 5.44 (dt, J = 16.0, 6.8 Hz, 1H), 5.20 (q, J = 7.1 Hz, 1H), 3.96 (d, J = 14.5 Hz, 1H),
3.70-3.56 (m, 4H), 3.63 (s, 3H), 3.59 (d, J = 13.7 Hz, 1H), 3.24 (d, J = 13.8 Hz, 1H), 2.90 (d, J =
14.6 Hz, 1H), 2.11 (q, J = 6.8 Hz, 1H), 1.80 (s, 3H), 1.46 (s, 9H), 1.41 (d, J = 7.0 Hz, 3H), 1.36-
192