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(b) For a disscusion on the stereoselectivity of allyltrimethylsilane α-amidoalkylations to related -phenylglycinol- or-1-phenylethylamine-derived δ- and γ-lactams, see: Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215-223.
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Interestingly, the reaction of 1 with PrMgBr takes place with opposite diastereoselectivity to give piperidone 5b as the major product: see ref 10c
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(e) Interestingly, the reaction of 1 with PrMgBr takes place with opposite diastereoselectivity to give piperidone 5b as the major product: see ref 10c.
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47
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0242497177
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For a preliminary account of this part of the work, see ref 9a
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For a preliminary account of this part of the work, see ref 9a.
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In the major isomers a the methine benzylic proton appears more shielded, and both the benzylic and C-6 carbons more deshielded, than in the minor isomers b
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(a) In the major isomers a the methine benzylic proton appears more shielded, and both the benzylic and C-6 carbons more deshielded, than in the minor isomers b
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58
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(a) For related approaches, involving the reductive ring-opening of phenylglycinol-derived 8a-substituted bicyclic δ-lactams, see: Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085.
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(a) For the opening of hexahydrooxazolo[3,2-a]pyridines with Grignard reagents, see: Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
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(c) For a study on the stereoselectivity of the reaction, see: Poerwono, H.; Higashiyama, K.; Yamauchi, T.; Kubo, H.; Ohmiya, S.; Takahashi, H. Tetrahedron 1998, 54, 13955-13970.
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2) is indicative of a 2,6-cis relationship, whereas the trans isomers show a slightly negative value: Yue, C.; Nicolay, J.-F.; Royer, J.; Husson, H.-P. Tetrahedron 1994, 50, 3139-3148.
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To avoid confusion with other reports, it must be noted that, according to the IUPAC recommendations, we assign the lower locant (i.e., 2) to the chain that should be cited first in the name (i.e., methyl)
-
(a) To avoid confusion with other reports, it must be noted that, according to the IUPAC recommendations, we assign the lower locant (i.e., 2) to the chain that should be cited first in the name (i.e., methyl).
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-
-
-
75
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0242413934
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23a,b and that, therefore, dihydropinidine is levorotatory. There is also a confusion in the literature in this respect
-
23a,b and that, therefore, dihydropinidine is levorotatory. There is also a confusion in the literature in this respect.
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-
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76
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0034595784
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(a) For recent enantioselective syntheses of dihydropinidine, see: Ciblat, S.; Besse, P.; Papastergiou, V.; Veschambre, H.; Canet, J.-L.; Troin, Y. Tetrahedron: Asymmetry 2000, 11, 2221-2229.
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(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 2221-2229
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Ciblat, S.1
Besse, P.2
Papastergiou, V.3
Veschambre, H.4
Canet, J.-L.5
Troin, Y.6
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77
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0035833078
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-
See also ref 14a and references cited therein
-
(b) Fréville, S.; Delbecq, P.; Thuy, V. M.; Petit, H.; Célérier, J. P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 4609-4611. See also ref 14a and references cited therein.
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(2001)
Tetrahedron Lett.
, vol.42
, pp. 4609-4611
-
-
Fréville, S.1
Delbecq, P.2
Thuy, V.M.3
Petit, H.4
Célérier, J.P.5
Lhommet, G.6
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80
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-
0034707982
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-
(a) For recent enantioselective syntheses of indolizidine 167B, see: Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465-467.
-
(2000)
Org. Lett.
, vol.2
, pp. 465-467
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Yamazaki, N.1
Ito, T.2
Kibayashi, C.3
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83
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0037119739
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(d) Zaminer, J.; Stapper, C.; Blechert, S. Tetrahedron Lett. 2002, 43, 6739-6741.
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 6739-6741
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-
Zaminer, J.1
Stapper, C.2
Blechert, S.3
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84
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0001324552
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(a) Isolation: Ritter, F. J.; Rotgans, I. E. M.; Talman, E.; Verwiel, P. E. J.; Stein, F. Experientia 1973, 29, 530-531.
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(1973)
Experientia
, vol.29
, pp. 530-531
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Ritter, F.J.1
Rotgans, I.E.M.2
Talman, E.3
Verwiel, P.E.J.4
Stein, F.5
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86
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-
0242497174
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-
Attempts to generate a Grignard reagent from several 1-halo-3-heptanone acetals were unsuccessful
-
Attempts to generate a Grignard reagent from several 1-halo-3-heptanone acetals were unsuccessful.
-
-
-
-
87
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-
0001738217
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-
See also ref 29b
-
This stereoselective cyclization has previously been reported: Yamaguchi, R.; Hata, E.; Matsuki, T.; Kawanisi, M. J. Org. Chem. 1987, 52, 2094-2096. See also ref 29b.
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(1987)
J. Org. Chem.
, vol.52
, pp. 2094-2096
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Yamaguchi, R.1
Hata, E.2
Matsuki, T.3
Kawanisi, M.4
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88
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-
0343899334
-
-
references cited therein
-
For previous enantioselective syntheses of monomorine I, see: Riesinger, S. W.; Löfstedt, J.; Pettersson-Fasth, H.; Bäckvall, J.-E. Eur. J. Org. Chem. 1999, 3277-3280 and references cited therein.
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(1999)
Eur. J. Org. Chem.
, pp. 3277-3280
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Riesinger, S.W.1
Löfstedt, J.2
Pettersson-Fasth, H.3
Bäckvall, J.-E.4
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89
-
-
0242581628
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-
3MgCl to give, after hydride reduction, trans-2,6-dimethylpiperidine 26 (R = H): see ref 16b
-
3MgCl to give, after hydride reduction, trans-2,6-dimethylpiperidine 26 (R = H): see ref 16b.
-
-
-
-
90
-
-
0032540967
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-
For a preliminary account of this part of the work, see: Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422.
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(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 2419-2422
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-
Amat, M.1
Hidalgo, J.2
Llor, N.3
Bosch, J.4
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91
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0001407663
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(a) Isolation: Kuzovkov, A. D.; Menshikov, G. P. Zh. Obshch. Khim. 1950, 20, 1524-1527; Chem. Abstr. 1951, 45, 2485g
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(1950)
Zh. Obshch. Khim.
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, pp. 1524-1527
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-
Kuzovkov, A.D.1
Menshikov, G.P.2
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92
-
-
4244118761
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-
(a) Isolation: Kuzovkov, A. D.; Menshikov, G. P. Zh. Obshch. Khim. 1950, 20, 1524-1527; Chem. Abstr. 1951, 45, 2485g
-
(1951)
Chem. Abstr.
, vol.45
-
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-
94
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0242497172
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-
It must be noted that lupetidine base is levorotatory
-
(c) It must be noted that lupetidine base is levorotatory.
-
-
-
-
95
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-
0025365335
-
-
See also ref 16b
-
(d) For previous enantioselective syntheses, see: Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279-3282. See also ref 16b.
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(1990)
Tetrahedron Lett.
, vol.3
, pp. 3279-3282
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-
Najdi, S.1
Kurth, M.J.2
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96
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0032971788
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-
See also ref 7e
-
(e) For the synthesis of ent-lupetidine (2S,6S), see: Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. Synth. Commun. 1999, 29, 1747-1756. See also ref 7e.
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(1999)
Synth. Commun.
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, pp. 1747-1756
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Adamo, M.F.A.1
Aggarwal, V.K.2
Sage, M.A.3
-
97
-
-
0000378926
-
-
(a) Isolation: MacConnell, J. G.; Blum, M. S.; Fales, H. M. Tetrahedron 1971, 26, 1129-1139.
-
(1971)
Tetrahedron
, vol.26
, pp. 1129-1139
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MacConnell, J.G.1
Blum, M.S.2
Fales, H.M.3
-
98
-
-
0028290706
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-
(b) Absolute configuration: Leclercq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Vander Meer, R.; Braekman, J. C. Tetrahedron 1994, 50, 8465-8478.
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(1994)
Tetrahedron
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, pp. 8465-8478
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-
Leclercq, S.1
Thirionet, I.2
Broeders, F.3
Daloze, D.4
Vander Meer, R.5
Braekman, J.C.6
-
99
-
-
0001114396
-
-
(a) The lower stereoselectivity in the hydride reduction of the C=N bond in related 1-piperidinium salts when R is an alkyl group larger than methyl has previously been reported: Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 2831-2843
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Maruoka, K.1
Miyazaki, T.2
Ando, M.3
Matsumura, Y.4
Sakane, S.5
Hattori, K.6
Yamamoto, H.7
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100
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0002809809
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(b) Ukaji, Y.; Watai, T.; Sumi, T.; Fujisawa, T. Chem. Lett. 1991, 1555-1558.
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(1991)
Chem. Lett.
, pp. 1555-1558
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Ukaji, Y.1
Watai, T.2
Sumi, T.3
Fujisawa, T.4
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101
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0242581627
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-
For previous enantioselective syntheses, see ref 14a and references cited therein
-
(a) For previous enantioselective syntheses, see ref 14a and references cited therein.
-
-
-
-
102
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0037015420
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(b) See also: Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459-3462.
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Org. Lett.
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, pp. 3459-3462
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Takahata, H.1
Ouchi, H.2
Ichinose, M.3
Nemoto, H.4
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103
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0043287627
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(c) For a review, see: Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proc. Int. 1996, 28, 499-543.
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(1996)
Org. Prep. Proc. Int.
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Leclercq, S.1
Daloze, D.2
Braekman, J.-C.3
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104
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33845375548
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(d) For the synthesis of the 2S,6S-enantiomer, see: Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477.
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J. Org. Chem.
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Grierson, D.S.1
Royer, J.2
Guerrier, L.3
Husson, H.-P.4
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105
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0030575797
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Amat, M.; Pshenichnyi, G.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 3091-3094.
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Tetrahedron: Asymmetry
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Amat, M.1
Pshenichnyi, G.2
Bosch, J.3
Molins, E.4
Miravitlles, C.5
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0001394411
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Poerwono, H.; Higashiyama, K.; Yamauchi, T.; Takahashi, H. Heterocycles 1997, 46, 385-400.
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Heterocycles
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Poerwono, H.1
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Takahashi, H.4
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0242665622
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Kunz, F.; Rétey, J.; Arigoni, D.; Tsai, L.; Stadtman, T. C. Helv. Chim. Acta 1978, 61, 1139-1145.
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Helv. Chim. Acta
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