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0038498498
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For previous applications of 5,6-dihydropyridin-2-ones in Diels-Alder reactions, see: (a) Casamitjana, N.; Amat, M.; Llor, N.; Carreras, M.; Pujol, X.; Fernández, M.; López, V.; Molins, E.; Miravitlles, C.; Bosch, J. Tetrahedron: Asymmetry 2003, 14, 2033-39.
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(a) Zhang, A. J.; Russell, D. H.; Zhu, J.; Burguess, K. Tetrahedron Lett. 1998, 39, 7439-7442.
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This reagent is compatible with the presence of other functional groups, see: (c) Hamada, Y.; Shiori, T. J. Org. Chem. 1986, 51, 5489-5490.
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0344127952
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note
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When N-deprotection was performed with TFA at 0 °C piperidone 6 was obtained in 63% yield accompanied by 3-(benzyloxycarbonyl)piperidin-2-one (13%) as a byproduct, see Experimental Section.
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(e) Macor, J. E.; Blank, D. H.; Ryan, K.; Post, R. J. Synthesis 1997, 443-449.
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(a) Shiori, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
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(c) Yamada, S.; Ninomiya, K.; Shiori, T. Tetrahedron 1974, 30, 2151-2157.
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3 failed, see: Fukazawa, T.; Shimoji, Y.; Hashimoto, T. Tetrahedron: Asymmetry 1996, 7, 1649-1658.
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Fukazawa, T.1
Shimoji, Y.2
Hashimoto, T.3
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38
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2642676149
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To obtain the carbamate with the amino group protected with Fmoc, (9-fluorenyl)methanol was used, instead of BnOH, but the reaction failed, see: Evans, D. A.; Black, C. J. Am. Chem. Soc. 1993, 115, 4497-4513.
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Altmann, K.-H.; Kesselring, R.; Pieles, U. Tetrahedron 1996, 52, 12699-12722.
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Altmann, K.-H.1
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Pieles, U.3
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40
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0344990548
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note
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2 in AcOEt at room temperature.
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42
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0025313287
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Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068-3074.
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(a) Nowick, J. S.; Smith, E. M.; F'airish, M. Chem. Soc. Rev. 1996, 25, 401-415.
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Lippens, G.1
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46
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0032864224
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(a) Brickman, K.; Yuan, Z.; Sethor, I.; Somfai, P.; Kihlberg, J. Chem. Eur. J. 1999, 5, 2241-2253.
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Lindvall, M.K.1
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Belvisi, L.1
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49
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0034005654
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(d) Belvisi, L.; Gennari, C.; Madder, A.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 695-699.
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Scolastico, C.6
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Scolastico, C.5
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51
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0040154253
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i+3 and the dihedral angle τ (-90° < τ < 90° formed by the four Cα atoms belonging to the tetrapeptide, see: Perczel, A.; McAllister, M. A.; Csaszar, P.; Csizmadia, I. G. J. Am. Chem. Soc. 1993, 115, 4849-4858.
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52
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0021779081
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The major β-turns are classified according to the torsion angles of the second (φ1, ψ1: φ1 = -60 ± 30° and ψ1 = 120 ± 30°) and third amino acids (φ2, ψ2: φ2 = 80 ± 30° and ψ2 = 0 ± 45°), see: (a) Rose, G. D.; Gierash, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109.
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Rose, G.D.1
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53
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0027231813
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(b) Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467-3478.
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Ball, J.B.1
Hughes, R.A.2
Alewood, P.F.3
Andrews, P.R.4
-
55
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0344127948
-
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note
-
The main features characterizing a classical γ-turn are the torsion angles of the second amino acid (φ2, ψ2: φ2 = 70°/85° and ψ2 = -60°/-70°) and the distance between the carbonyl carbon atom of the second amino acid (i+1) and the nitrogen atom of the amino group of the third residue (i+3) with a preferential value of 3 Å, see ref 27a.
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-
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59
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0020163940
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The temperature coefficients in DMSO, according to Kessler criteria, suggested that in diastereomer I protons NHa and NHc (|Δδ/ΔT| < 3 ppb/K) were intramolecularly hydrogen bonded whereas protons NHb and NHd (|Δδ/ΔT| ∼ 4 ppb/K) were exposed to the solvent. For diastereomer II, proton NHa (|Δδ/ΔT| = 2.5 ppb/K) was probably intramolecularly hydrogen bonded whereas other NH protons were exposed to the solvent (Table 1), see: Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
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Kessler, H.1
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60
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0344990547
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note
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The above results were confirmed performing a parallel conformational search, using molecular dynamics with Iterative Simulated Annealing, see ref 36. This protocol was run five times, employing fully extended starting structures of both compounds (17a and 17b) and AMBER (implemented in DISCOVER 3) as force field. The profiles for the main parameters characterizing γ- and β-turns were similar to those found with the Monte Carlo protocol (data not shown).
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62
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0004148050
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Hehre, W. J.; Huang, W. W.; Klunzinger, P. E.; Deppmeier, B. J.; Driessen, A. J. A Spartan Tutorial; Wavefunction, Inc.: Irvine, CA, 1997; pp 85-93.
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Hehre, W.J.1
Huang, W.W.2
Klunzinger, P.E.3
Deppmeier, B.J.4
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64
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0033617241
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Toshima, H.; Maru, K.; Saito, M.; Ichihara, A. Tetrahedron 1999, 55, 5793-5808.
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Toshima, H.1
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Saito, M.3
Ichihara, A.4
-
65
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0345421633
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note
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Proton 4-H could not be assigned because it is masked by signals corresponding to the major isomer trans-9a.
-
-
-
-
66
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0345421634
-
-
note
-
13C NMR spectra indicated the presence of rotamers. This fact was not observed for the cis isomer.
-
-
-
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67
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0344559478
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-
note
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Rotamers were observed.
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|