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62349084965
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4. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (generally hexane-EtOAc, 8:2).
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4. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography (generally hexane-EtOAc, 8:2).
-
-
-
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43
-
-
62349106966
-
-
Data for Selected Compound: (2S,4S, Di-tert-butyl 6-Oxo-4-phenylpiperidine-1,2-dicarboxylate (4a) From 3a (119 mg, 0.32 mmol) was obtained 4a as a white solid (120 mg, 100, α]D -28.6 (c 1.04, CHCl 3, mp 142.5-147.5°C. IR (KBr, 2982, 2934, 1731, 1703, 1605, 1495, 1473, 1459, 1392, 1365, 1283, 1270, 1237, 1153, 1135, 1099, 1042, 1029, 1015 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.37 (t, 2 H, J, 7.2 Hz, 7.29 (t, 1 H, J, 7.4 Hz, 7.21 (d, 2 H, J, 7.2 Hz, 4.60 (dd, 1 H, J, 10.0, 6.6 Hz, 3.17-3.08 (m, 1 H, 2.85-2.79 (m, 1 H, 2.64 (dd, 1 H, J, 16.8, 13.0 Hz, 2.59-2.52 (m, 1 H, 2.03-1.94 (m, 1 H, 1.56 (s, 9 H, 1.48 (s, 9 H) ppm. 13C NMR 100 MHz, CDCl3, δ, 170.2, 169.6, 152.1, 141.7, 128.6, 126.9, 126.1, 83.4, 81.9, 58.7, 41.5, 36.7, 33.4, 27.5 ppm. HRMS: m/z cal
-
+.
-
-
-
-
44
-
-
33746326836
-
-
(a) Knor, S.; Laufer, B.; Kessler, H. J. Org. Chem. 2006, 71, 5625.
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J. Org. Chem
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Knor, S.1
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45
-
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33845220053
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(b) Torrado, M.; Masaguer, C. F.; Raviña, E. Tetrahedron Lett. 2007, 48, 323.
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Torrado, M.1
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50
-
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0347411032
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Wallace, D. J.; Klauber, D. J.; Chen, C. Y.; Volante, R. P. Org. Lett. 2003, 5, 4749.
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Wallace, D.J.1
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-
51
-
-
62349092091
-
-
Data for Selected Compound: (2S,4S,5R)-Di-tert-butyl 5-Allyl-6-oxo-4- phenylpiperidine-1,2-dicarboxylate (5) From 4a (1.06 g, 2.82 mmol) was obtained 5 as a white solid (904 mg, 77, α]D -133.1 (c 1.41, CHCl3, mp 115-117°C. IR (KBr, 2980, 1728, 1707, 1457, 1366, 1283, 1248, 1225, 1145, 1028 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.36-7.28 (m, 2 H, 7.28-7.20 (m, 1 H, 7.18-7.08 (m, 2 H, 5.70 (dddd, 1 H, J, 17.0, 10.1, 8.6, 5.7 Hz, 4.97 (d, 1 H, J, 10.1 Hz, 4.85 (d, 1 H, J, 17.1 Hz, 4.47 (dd, 1 H, J, 10.3, 6.2 Hz, 2.92 (dt, 1 H, J, 11.8, 11.8, 3.9 Hz, 2.73 (td, 1 H, J, 11.9, 4.5, 4.5 Hz, 2.66-2.51 (m, 1 H, 2.38 (ddd, 1 H, J, 13.7, 6.1, 4.0 Hz, 2.06-1.93 (m, 2 H, 1.51 (s, 9 H, 1.42 (s, 9 H) ppm. 13C NMR 75 MHz, CDCl3, δ, 171.8, 170
-
+.
-
-
-
-
52
-
-
62349094023
-
-
Data for Selected Compound: (2S,4R, Di-tert-butyl 4-Phenylpiperidine-1,2-dicarboxylate (8) From 4a (30 mg, 0.08 mmol) was obtained 8 as a colorless gum (25 mg, 93, α]D -15.6 (c 0.95, CHCl3, IR (NaCl, 2976, 1738, 1699, 1602, 1478, 1454, 1393, 1366, 1249, 1150, 1028 cm -1. 1H NMR (400 MHz, CDCl3, δ (rotamers, 7.35-7.31 (m, 2 H, 7.26-7.21 (m, 3 H, 4.25-4.21 (m, 1 H, 3.75-3.56 (m, 2 H, 2.88-2.80 (m, 1 H, 2.28-2.22 (m, 1 H, 2.14-2.02 (m, 2 H, 1.87-1.78 (m, 1 H, 1.49 (s, 9 H, 1.42 (s, 9 H, 13C 100 MHz, CDCl3, δ, 171.3, 155.4, 144.6, 128.2, 126.6, 126.0, 80.6, 79.7, 56.1, 37.1, 32.4, 29.8, 28.0, 27.6 ppm. HRMS: m/z calcd for C21H 31NO4: 361.22531; found: 362.23232 [M, H
-
+.
-
-
-
-
54
-
-
0141566578
-
-
(b) Hanessian, S.; Papeo, G.; Angiolini, M.; Fettis, K.; Beretta, M.; Munro, A. J. Org. Chem. 2003, 68, 7204.
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Hanessian, S.1
Tremblay, M.2
Marzi, M.3
Del Valle, J.R.4
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