-
1
-
-
0037014040
-
-
For some elegant examples of natural product synthesis featuring tetrahydropyridines as nucleophilic key intermediates, see: Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945; Jakubowicz, K.; Ben Abdelgelil, K.; Herdemann, M.; Martin, M.-T. ; Gateau-Olesker, A.; Al Mourabit, A.; Marazano, C.; Das, B. C. J. Org. Chem. 1999, 64, 7381-7387. Wanner, M. J.; Koomen, G.-J. J. Org. Chem. 1995, 60, 5634-5637.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 1941-1945
-
-
Nicolaou, K.C.1
Nevalainen, M.2
Safina, B.S.3
Zak, M.4
Bulat, S.5
-
2
-
-
0033214301
-
-
For some elegant examples of natural product synthesis featuring tetrahydropyridines as nucleophilic key intermediates, see: Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945; Jakubowicz, K.; Ben Abdelgelil, K.; Herdemann, M.; Martin, M.-T. ; Gateau-Olesker, A.; Al Mourabit, A.; Marazano, C.; Das, B. C. J. Org. Chem. 1999, 64, 7381-7387. Wanner, M. J.; Koomen, G.-J. J. Org. Chem. 1995, 60, 5634-5637.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7381-7387
-
-
Jakubowicz, K.1
Ben Abdelgelil, K.2
Herdemann, M.3
Martin, M.-T.4
Gateau-Olesker, A.5
Al Mourabit, A.6
Marazano, C.7
Das, B.C.8
-
3
-
-
0029116994
-
-
For some elegant examples of natural product synthesis featuring tetrahydropyridines as nucleophilic key intermediates, see: Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941-1945; Jakubowicz, K.; Ben Abdelgelil, K.; Herdemann, M.; Martin, M.-T. ; Gateau-Olesker, A.; Al Mourabit, A.; Marazano, C.; Das, B. C. J. Org. Chem. 1999, 64, 7381-7387. Wanner, M. J.; Koomen, G.-J. J. Org. Chem. 1995, 60, 5634-5637.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 5634-5637
-
-
Wanner, M.J.1
Koomen, G.-J.2
-
4
-
-
0042865038
-
-
For preliminary results, see: François, D.; Poupon, E.; Lallemand, M.-C.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 2000, 65, 3209-3212.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3209-3212
-
-
François, D.1
Poupon, E.2
Lallemand, M.-C.3
Kunesch, N.4
Husson, H.-P.5
-
5
-
-
84981757172
-
-
(a) Schöpf, C.; Arm, H.; Braun, F. Chem. Ber. 1952, 85, 937-948.
-
(1952)
Chem. Ber.
, vol.85
, pp. 937-948
-
-
Schöpf, C.1
Arm, H.2
Braun, F.3
-
9
-
-
0034678589
-
-
Poupon, E.; Kunesch, N.; Husson, H.-P. Ang. Chem., Int. Ed. 2000, 39, 1493-1495.
-
(2000)
Ang. Chem., Int. Ed.
, vol.39
, pp. 1493-1495
-
-
Poupon, E.1
Kunesch, N.2
Husson, H.-P.3
-
10
-
-
85039529133
-
-
note
-
General and versatile asymmetric methods for synthesizing 3-substituted piperidines are by far less numerous compared to methodologies for access to 2-subsituted systems.
-
-
-
-
11
-
-
0033431540
-
-
For a comprehensive review on the CN(R,S) strategy see: Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383-394.
-
(1999)
Chem. Soc. Rev.
, vol.28
, pp. 383-394
-
-
Husson, H.-P.1
Royer, J.2
-
12
-
-
85039541614
-
-
note
-
See Supporting Information for an improved synthesis of building block 2.
-
-
-
-
13
-
-
0037541354
-
-
See inter alia: (a) Asymmetric Michael addition reactions involving chiral imines, reviews: Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690. Christoffers, J. Chem. Eur. J. 2003, 9, 4862-4867. D'Angelo, J.; Desmaële, D.; Dumas, F.; Guinguant, A. Tetrahedron: Asymmetry 1992, 3, 459-505.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1688-1690
-
-
Christoffers, J.1
Baro, A.2
-
14
-
-
0142228974
-
-
See inter alia: (a) Asymmetric Michael addition reactions involving chiral imines, reviews: Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690. Christoffers, J. Chem. Eur. J. 2003, 9, 4862-4867. D'Angelo, J.; Desmaële, D.; Dumas, F.; Guinguant, A. Tetrahedron: Asymmetry 1992, 3, 459-505.
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 4862-4867
-
-
Christoffers, J.1
-
15
-
-
0026561424
-
-
See inter alia: (a) Asymmetric Michael addition reactions involving chiral imines, reviews: Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690. Christoffers, J. Chem. Eur. J. 2003, 9, 4862-4867. D'Angelo, J.; Desmaële, D.; Dumas, F.; Guinguant, A. Tetrahedron: Asymmetry 1992, 3, 459-505.
-
(1992)
Tetrahedron: Asymmetry
, vol.3
, pp. 459-505
-
-
D'Angelo, J.1
Desmaële, D.2
Dumas, F.3
Guinguant, A.4
-
18
-
-
0035968406
-
-
(d) Vázquez, E.; Galindo, A.; Gnecco, D.; Bernès, B. Tetrahedron: Asymmetry 2001, 12, 2099-2102.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 2099-2102
-
-
Vázquez, E.1
Galindo, A.2
Gnecco, D.3
Bernès, B.4
-
19
-
-
0001542017
-
-
For a leading reference, see: Stevens, R. V. Acc. Chem. Res. 1984, 17, 7, 289-296.
-
(1984)
Acc. Chem. Res.
, vol.17
, Issue.7
, pp. 289-296
-
-
Stevens, R.V.1
-
20
-
-
0034703296
-
-
Nitramine: see ref 15 and references therein. Serratezomine A: Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245. Gymnodimine: Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096. For the construction of the spirocyclic moiety: Yang, J.; Cohn, S. T.; Romo, D. Org. Lett. 2000, 2, 763-766. For racemic synthesis of the key pharmacophoric spirocyclic imine, see: Trzoss, M.; Brimble, M. A. Synlett 2003, 2042-2046.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6241-6245
-
-
Morita, H.1
Arisaka, M.2
Yoshida, N.3
Kobayashi, J.4
-
21
-
-
0029116303
-
-
Nitramine: see ref 15 and references therein. Serratezomine A: Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245. Gymnodimine: Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096. For the construction of the spirocyclic moiety: Yang, J.; Cohn, S. T.; Romo, D. Org. Lett. 2000, 2, 763-766. For racemic synthesis of the key pharmacophoric spirocyclic imine, see: Trzoss, M.; Brimble, M. A. Synlett 2003, 2042-2046.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 7093-7096
-
-
Seki, T.1
Satake, M.2
Mackenzie, L.3
Kaspar, H.F.4
Yasumoto, T.5
-
22
-
-
0034704624
-
-
Nitramine: see ref 15 and references therein. Serratezomine A: Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245. Gymnodimine: Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096. For the construction of the spirocyclic moiety: Yang, J.; Cohn, S. T.; Romo, D. Org. Lett. 2000, 2, 763-766. For racemic synthesis of the key pharmacophoric spirocyclic imine, see: Trzoss, M.; Brimble, M. A. Synlett 2003, 2042-2046.
-
(2000)
Org. Lett.
, vol.2
, pp. 763-766
-
-
Yang, J.1
Cohn, S.T.2
Romo, D.3
-
23
-
-
0242320442
-
-
Nitramine: see ref 15 and references therein. Serratezomine A: Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245. Gymnodimine: Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096. For the construction of the spirocyclic moiety: Yang, J.; Cohn, S. T.; Romo, D. Org. Lett. 2000, 2, 763-766. For racemic synthesis of the key pharmacophoric spirocyclic imine, see: Trzoss, M.; Brimble, M. A. Synlett 2003, 2042-2046.
-
(2003)
Synlett.
, pp. 2042-2046
-
-
Trzoss, M.1
Brimble, M.A.2
-
24
-
-
0032488588
-
-
Yang, L.; Morriello, G.; Prendergast, K.; Cheng, K.; Jacks, T.; Chan, W. W.-S.; Schleim, K. D.; Smith, R. G.; Patchett, A. Bioorg. Med. Chem. Lett. 1998, 8, 107-112.
-
(1998)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 107-112
-
-
Yang, L.1
Morriello, G.2
Prendergast, K.3
Cheng, K.4
Jacks, T.5
Chan, W.W.-S.6
Schleim, K.D.7
Smith, R.G.8
Patchett, A.9
-
25
-
-
0033966126
-
-
(a) GABA analogues: Bendl, M.; Eder, M.; Langhammer, I.; Urban, E. Heterocycles 2000, 53, 115-126.
-
(2000)
Heterocycles
, vol.53
, pp. 115-126
-
-
Bendl, M.1
Eder, M.2
Langhammer, I.3
Urban, E.4
-
26
-
-
0033575678
-
-
(b) Gabapentin analogues: Receveur, J.-M.; Bryans, J. S.; Field, M. J.; Singh, L.; Horwell, D. C. Bioorg. Med. Chem. Lett. 1999, 9, 2329-2334.
-
(1999)
Bioorg. Med. Chem. Lett.
, vol.9
, pp. 2329-2334
-
-
Receveur, J.-M.1
Bryans, J.S.2
Field, M.J.3
Singh, L.4
Horwell, D.C.5
-
27
-
-
0029082519
-
-
(c) GABA-uptake inhibitors: Fleischhacker, W.; Lauritz, S.; Urban, E.; Baurmann, P.; Bittiger, H. Eur. J. Med. Chem. 1995, 30, 707-713.
-
(1995)
Eur. J. Med. Chem.
, vol.30
, pp. 707-713
-
-
Fleischhacker, W.1
Lauritz, S.2
Urban, E.3
Baurmann, P.4
Bittiger, H.5
-
28
-
-
85039521296
-
-
U.S. Patent 4 374 991, 1983
-
(a) Smolanoff, J. U.S. Patent 4 374 991, 1983.
-
-
-
Smolanoff, J.1
-
29
-
-
85039515290
-
-
U.S. Patent 4 400 512, 1983
-
(b) Smolanoff, J. U.S. Patent 4 400 512, 1983.
-
-
-
Smolanoff, J.1
-
30
-
-
0031929582
-
-
François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Ang. Chem., Int. Ed. 1998, 37, 104-105.
-
(1998)
Ang. Chem., Int. Ed.
, vol.37
, pp. 104-105
-
-
François, D.1
Lallemand, M.-C.2
Selkti, M.3
Tomas, A.4
Kunesch, N.5
Husson, H.-P.6
-
31
-
-
0037239888
-
-
For recent examples of spirocyclic compounds constructed by the means of an enamine/Michael and aldol sequence, see: Christoffers, J.; Kreidler, B.; Oertling, H.; Unger, S.; Frey, W. Synlett 2003, 493-496. Christoffers, J.; Kreidler, B.; Unger, S.; Frey, W. Eur. J. Org. Chem. 2003, 2845-2853.
-
(2003)
Synlett.
, pp. 493-496
-
-
Christoffers, J.1
Kreidler, B.2
Oertling, H.3
Unger, S.4
Frey, W.5
-
32
-
-
0041654776
-
-
For recent examples of spirocyclic compounds constructed by the means of an enamine/Michael and aldol sequence, see: Christoffers, J.; Kreidler, B.; Oertling, H.; Unger, S.; Frey, W. Synlett 2003, 493-496. Christoffers, J.; Kreidler, B.; Unger, S.; Frey, W. Eur. J. Org. Chem. 2003, 2845-2853.
-
(2003)
Eur. J. Org. Chem.
, pp. 2845-2853
-
-
Christoffers, J.1
Kreidler, B.2
Unger, S.3
Frey, W.4
-
33
-
-
85039522357
-
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note
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See ref 5 for examples.
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-
-
34
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-
2442678446
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-
For examples, see the following. (a) For the preparation of racemic 3-thiopiperidines: Ibarra, C. A.; Cuervo, R.; Fernández-Monreal, M. C.; García, M.; Ruiz, M. P.; Elliel, E. L. J. Chem. Soc., Perkin Trans 1 1991, 1473-1477.
-
(1991)
J. Chem. Soc., Perkin Trans 1
, pp. 1473-1477
-
-
Ibarra, C.A.1
Cuervo, R.2
Fernández-Monreal, M.C.3
García, M.4
Ruiz, M.P.5
Elliel, E.L.6
-
35
-
-
0345435969
-
-
(b) For enantioselective strategy starting from a lactam derived from (R)-(-)-phenylglycinol, see: Forns, P.; Montserrat Fernández, M.; Diez, A.; Rubiralta, M.; Cherrier, M.-P.; Bonin, M.; Quirion, J.-C. Synthesis 1999, 258-263.
-
(1999)
Synthesis
, pp. 258-263
-
-
Forns, P.1
Montserrat Fernández, M.2
Diez, A.3
Rubiralta, M.4
Cherrier, M.-P.5
Bonin, M.6
Quirion, J.-C.7
-
37
-
-
85039539670
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note
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Mechanistic considerations for the ready formation of this 4-oxo-1-azabicyclo[3.3.1]nonane derivative are discussed in Supporting Information.
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-
-
38
-
-
0038345080
-
-
Langille, N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2003, 5, 575-578.
-
(2003)
Org. Lett.
, vol.5
, pp. 575-578
-
-
Langille, N.F.1
Dakin, L.A.2
Panek, J.S.3
-
39
-
-
0037459890
-
-
Recent reviews in the field of piperidines and piperidones: (a) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989.
-
(2003)
Tetrahedron
, vol.59
, pp. 2953-2989
-
-
Weintraub, P.M.1
Sabol, J.S.2
Kane, J.M.3
Borcherding, D.R.4
-
41
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85039534128
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note
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13C NMR, COSY, HETCOR and, when needed, NOESY experiments.
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