-
1
-
-
0842268019
-
-
For recent reviews on the stereoselective synthesis of piperidines, see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701-1729.
-
(2004)
Tetrahedron
, vol.60
, pp. 1701-1729
-
-
Buffat, M.G.P.1
-
3
-
-
0037459890
-
-
(c) 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
-
4
-
-
14544284028
-
-
For recent examples: (a) Wang, X.; Dong, Y.; Sun, J.; Xu, X.; Li, R.; Hu, Y. J. Org. Chem. 2005, 70, 1897-1900.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 1897-1900
-
-
Wang, X.1
Dong, Y.2
Sun, J.3
Xu, X.4
Li, R.5
Hu, Y.6
-
5
-
-
4544313802
-
-
(b) Toure, B. B.; Hall, D. G. Angew. Chem., Int. Ed. 2004, 43, 2001-2004.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 2001-2004
-
-
Toure, B.B.1
Hall, D.G.2
-
6
-
-
4644272647
-
-
(c) Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808-11809.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11808-11809
-
-
Ichikawa, E.1
Suzuki, M.2
Yabu, K.3
Albert, M.4
Kanai, M.5
Shibasaki, M.6
-
7
-
-
2442720188
-
-
(d) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240-6241.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 6240-6241
-
-
Shintani, R.1
Tokunaga, N.2
Doi, H.3
Hayashi, T.4
-
8
-
-
0000309769
-
-
See also: (e) Comins, D. L.; Goehring, R. R.; Joseph, S. P.; O'Connor, S. J. Org. Chem. 1990, 55, 2574-2576.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2574-2576
-
-
Comins, D.L.1
Goehring, R.R.2
Joseph, S.P.3
O'Connor, S.4
-
9
-
-
0027285071
-
-
(f) Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052-2057.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 2052-2057
-
-
Génisson, Y.1
Marazano, C.2
Das, B.C.3
-
10
-
-
0342951124
-
-
Brossi, A., Ed.; Academic Press: New York, Chapter 3
-
(a) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, Chapter 3.
-
(1985)
The Alkaloids
, vol.26
-
-
Strunz, G.M.1
Findlay, J.A.2
-
11
-
-
0033063858
-
-
(b) Astudillo S. L.; Jürgens, S. K.; Schmeda-Hirschmann, G.; Griffith, G. A.; Holt, D. J.; Jenkins, P. R. Planta Med. 1999, 65, 161-162.
-
(1999)
Planta Med.
, vol.65
, pp. 161-162
-
-
Astudillo, S.L.1
Jürgens, S.K.2
Schmeda-Hirschmann, G.3
Griffith, G.A.4
Holt, D.J.5
Jenkins, P.R.6
-
13
-
-
0029042112
-
-
(d) Bolzani, V. S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929-5934.
-
(1995)
Tetrahedron
, vol.51
, pp. 5929-5934
-
-
Bolzani, V.S.1
Gunatilaka, A.A.L.2
Kingston, D.G.I.3
-
14
-
-
0000656741
-
-
(e) Hootelé, C.; Colau, B.; Halin, F. Tetrahedron Lett. 1980, 21, 5061-5062.
-
(1980)
Tetrahedron Lett.
, vol.21
, pp. 5061-5062
-
-
Hootelé, C.1
Colau, B.2
Halin, F.3
-
15
-
-
0000904923
-
-
(f) Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379-423.
-
(1983)
Chem. Rev.
, vol.83
, pp. 379-423
-
-
Baliah, V.1
Jeyaraman, R.2
Chandrasekaran, L.3
-
20
-
-
4344693778
-
-
Liu, L.-X.; Ruan, Y.-P.; Guo, Z.-Q.; Huang, P.-Q. J. Org. Chem. 2004, 69, 6001-6009.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6001-6009
-
-
Liu, L.-X.1
Ruan, Y.-P.2
Guo, Z.-Q.3
Huang, P.-Q.4
-
22
-
-
0012843055
-
-
(f) Makabe, H.; Kong, L. K.; Hirota, M. Org. Lett. 2003, 5, 27-29.
-
(2003)
Org. Lett.
, vol.5
, pp. 27-29
-
-
Makabe, H.1
Kong, L.K.2
Hirota, M.3
-
23
-
-
0242543832
-
-
(g) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839-3842.
-
(2003)
Org. Lett.
, vol.5
, pp. 3839-3842
-
-
Sato, T.1
Aoyagi, S.2
Kibayashi, C.3
-
24
-
-
0041743187
-
-
(h) Lee, H. K.; Chun, J. S.; Pak, C. S. Tetrahedron 2003, 59, 6445-6454.
-
(2003)
Tetrahedron
, vol.59
, pp. 6445-6454
-
-
Lee, H.K.1
Chun, J.S.2
Pak, C.S.3
-
26
-
-
0242543805
-
-
(j) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855-3857.
-
(2003)
Org. Lett.
, vol.5
, pp. 3855-3857
-
-
Davis, F.A.1
Rao, A.2
Carroll, P.J.3
-
30
-
-
0037017027
-
-
(n) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron, Lett. 2002, 43, 1071-1074.
-
(2002)
Tetrahedron, Lett.
, vol.43
, pp. 1071-1074
-
-
Bailey, P.D.1
Smith, P.D.2
Morgan, K.M.3
Rosair, G.M.4
-
31
-
-
0035812743
-
-
(o) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829-6832.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6829-6832
-
-
Comins, D.L.1
Sandelier, M.J.2
Grillo, T.A.3
-
33
-
-
0032560720
-
-
(q) Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796.
-
(1998)
Tetrahedron
, vol.54
, pp. 8783-8796
-
-
Agami, C.1
Couty, F.2
Lam, H.3
Mathieu, H.4
-
34
-
-
0032542173
-
-
and references therein
-
(r) Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
-
(1998)
Tetrahedron
, vol.54
, pp. 15589-15606
-
-
Kiguchi, T.1
Shirakawa, M.2
Honda, R.3
Ninomiya, I.4
Naito, T.5
-
35
-
-
0035965734
-
-
(a) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 11829-11830
-
-
Charette, A.B.1
Grenon, M.2
Lemire, A.3
Pourashraf, M.4
Martel, J.5
-
37
-
-
6444238793
-
-
(c) Lemire, A.; Grenon, M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517-3520.
-
(2004)
Org. Lett.
, vol.6
, pp. 3517-3520
-
-
Lemire, A.1
Grenon, M.2
Pourashraf, M.3
Charette, A.B.4
-
38
-
-
15444361998
-
-
(d) Lemire, A.; Beaudoin, D.; Grenon, M.; Charette, A. B. J. Org. Chem. 2005, 70, 2368-2371.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2368-2371
-
-
Lemire, A.1
Beaudoin, D.2
Grenon, M.3
Charette, A.B.4
-
39
-
-
0000129968
-
-
Moody, C. J., Ed.; JAI Press, Inc.: Greenwich, CT
-
(a) Comins, D. L.; Joseph, S. P. Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press, Inc.: Greenwich, CT, 1996; Vol. 2, pp 251-294.
-
(1996)
Advances in Nitrogen Heterocycles
, vol.2
, pp. 251-294
-
-
Comins, D.L.1
Joseph, S.P.2
-
41
-
-
33748542524
-
-
(c) Johnson, F. Chem. Rev. 1968, 68, 375-413.
-
(1968)
Chem. Rev.
, vol.68
, pp. 375-413
-
-
Johnson, F.1
-
42
-
-
0035053652
-
-
For a review on stereocontrolled additions to di- and tetrahydropyridines, see: (a) Kumar, R.; Chandra, R. Adv. Heterocycl. Chem. 2001, 78, 269-313.
-
(2001)
Adv. Heterocycl. Chem.
, vol.78
, pp. 269-313
-
-
Kumar, R.1
Chandra, R.2
-
44
-
-
0037460173
-
-
For stereoselective synthesis of 1,2,5,6-tetrahydropyridines, see: (c) Huang, H.; Spande, T. F.; Panek, J. S. J. Am. Chem. Soc. 2003, 125, 626-627.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 626-627
-
-
Huang, H.1
Spande, T.F.2
Panek, J.S.3
-
46
-
-
0000581455
-
-
For 2,6-disubstituted 1,2-dihydropyridines, see: (a) Comins, D. L.; Weglarz, M. A. J. Org. Chem. 1991, 56, 2506-2512.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2506-2512
-
-
Comins, D.L.1
Weglarz, M.A.2
-
47
-
-
0000111986
-
-
(b) Yamaguchi, R.; Nakazono, Y.; Matsuki, T.; Hata, E.-i.; Kawanisi, M. Bull Chem. Soc. Jpn. 1987, 60, 215-222.
-
(1987)
Bull Chem. Soc. Jpn.
, vol.60
, pp. 215-222
-
-
Yamaguchi, R.1
Nakazono, Y.2
Matsuki, T.3
Hata, E.-I.4
Kawanisi, M.5
-
48
-
-
0035807531
-
-
For 3,5-disubstituted dihydropyridines, see: (c) Comins, D. L.; Williams, A. L. Org. Lett. 2001, 3, 3217-3220.
-
(2001)
Org. Lett.
, vol.3
, pp. 3217-3220
-
-
Comins, D.L.1
Williams, A.L.2
-
49
-
-
0035835945
-
-
For disubstituted 1,2-dihydropyridines substituted with an electron-withdrawing group, see: (a) Kita, Y.; Maekawa, H.; Yamasaki, Y.; Nishiguchi, I. Tetrahedron 2001, 57, 2095-2102.
-
(2001)
Tetrahedron
, vol.57
, pp. 2095-2102
-
-
Kita, Y.1
Maekawa, H.2
Yamasaki, Y.3
Nishiguchi, I.4
-
50
-
-
0028264817
-
-
(b) Lavilla, R.; Gotsens, T.; Gullón, F.; Bosch, J. Tetrahedron 1994, 50, 5233-5244.
-
(1994)
Tetrahedron
, vol.50
, pp. 5233-5244
-
-
Lavilla, R.1
Gotsens, T.2
Gullón, F.3
Bosch, J.4
-
51
-
-
29844452574
-
-
(c) Naito, T.; Lida, N.; Ninomiya, I. J. Chem. Soc., Perkin Trans. 1 1986, 99-104.
-
(1986)
J. Chem. Soc., Perkin Trans. 1
, pp. 99-104
-
-
Naito, T.1
Lida, N.2
Ninomiya, I.3
-
52
-
-
0000044060
-
-
Camps, F.; Coll, J.; Messeauer, A.; Pujol, F. J. Org. Chem. 1982, 47, 5402-5404. 2-Propanol was used as a nucleophile since methanol is described to be incompatible with this epoxidation procedure. Furthermore, both nucleophiles were shown to cleanly react with 12 (with DMDO, see Table 2).
-
(1982)
Org. Chem.
, vol.47
, pp. 5402-5404
-
-
Camps, F.1
Coll, J.2
Messeauer, A.3
Pujol, F.J.4
-
53
-
-
0028151122
-
-
This KF-MCPBA complex was shown to cleanly epoxidize diverse glucals; see: Bellucci, G.; Catelani, G.; Chiappe, C.; D'Andrea, F. Tetrahedron Lett. 1994, 35, 8433-8436.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 8433-8436
-
-
Bellucci, G.1
Catelani, G.2
Chiappe, C.3
D'Andrea, F.4
-
54
-
-
29844433950
-
-
note
-
Cis product is the kinetic product since treatment of 13a with TFA in EtOH for 76 h led to the 2,3-trans-ethanol adduct in 74% yield.
-
-
-
-
55
-
-
12344325648
-
-
Blaauw and co-workers reported an oxone-mediated epoxidation-methanol opening of a related tetrahydropyridine, but the cis-trans ratio was not specified. See: Botman, P. N. M.; Dommerholt, F. J.; de Gelder, R.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T.; Blaauw, R. H. Org. Lett. 2004, 6, 4941-4944.
-
(2004)
Org. Lett.
, vol.6
, pp. 4941-4944
-
-
Botman, P.N.M.1
Dommerholt, F.J.2
De Gelder, R.3
Broxterman, Q.B.4
Schoemaker, H.E.5
Rutjes, F.P.J.T.6
Blaauw, R.H.7
-
56
-
-
0035909621
-
-
Related cis stereoselective pyridinone epoxide intramolecular opening with an alcohol, leading to an oxazolopiperidine, has been reported: Amat, M.; Llor, N.; Huguet, M.; Molins, E.; Espinosa, E.; Bosch, J. Org. Lett. 2001, 3, 3257-3260.
-
(2001)
Org. Lett.
, vol.3
, pp. 3257-3260
-
-
Amat, M.1
Llor, N.2
Huguet, M.3
Molins, E.4
Espinosa, E.5
Bosch, J.6
-
57
-
-
0032569868
-
-
Asymmetric epoxidation of unsubstituted N-tosyl-1,4,5,6- tetrahydropyridirines has been reported, but the yields or enantioselectivities are modest; see: Sunose, M.; Anderson, K. M.; Orpen, A. G.; Gallagher, T.; Macdonald, S. J. F. Tetrahedron Lett. 1998, 39, 8885-8888.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8885-8888
-
-
Sunose, M.1
Anderson, K.M.2
Orpen, A.G.3
Gallagher, T.4
Macdonald, S.J.F.5
-
58
-
-
0032554991
-
-
DMDO and MCPBA epoxidation of unsubstituted N-ethylcarbamoyl-1,4,5,6- tetrahydropyridines has been reported, but the cis-trans selectivity of the nucleophilic substitution of the epoxide is low (1:1.5 to 1:1.8), see: (a) Sugisaki, C. H.; Carroll, P. J.; Correia, C. R. D. Tetrahedron Lett. 1998, 39, 3413-3416.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 3413-3416
-
-
Sugisaki, C.H.1
Carroll, P.J.2
Correia, C.R.D.3
-
59
-
-
0029880759
-
-
(b) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255-3258.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 3255-3258
-
-
Burgess, L.E.1
Gross, E.K.M.2
Jurka, J.3
-
60
-
-
0005200995
-
-
(a) Treatment of N-acetyl-1,4,5,6-tetrahydropyridines with peroxybenzoic acid gave N-acetyl-2-benzoyloxy-3-hydroxypiperidine, but the cis-trans ratio was not specified; see: Masamune, T.; Hayashi, H.; Takasugi, M.; Fukuoka, S. J. Org. Chem. 1972, 57, 2343-2345.
-
(1972)
J. Org. Chem.
, vol.57
, pp. 2343-2345
-
-
Masamune, T.1
Hayashi, H.2
Takasugi, M.3
Fukuoka, S.4
-
61
-
-
0032567316
-
-
(b) A related MCPBA epoxidation of N-methylcarbamoyl-1,4-dihydropyridine has been shown to give the corresponding addition products with trans relative stereochemistry. However, use of DMDO afforded a dioxane dimer from dimerization of the opened epoxide; see: Lavilla, R.; Barón, X.; Coll, O.; Gullón, F.; Masdeu, C.; Bosch, J. J. Org. Chem. 1998, 63, 10001-10005.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 10001-10005
-
-
Lavilla, R.1
Barón, X.2
Coll, O.3
Gullón, F.4
Masdeu, C.5
Bosch, J.6
-
62
-
-
0037955984
-
-
For a related cis stereoselective glycal epoxide opening using organozinc triflate or organozinc chloride, see: Xue, S.; Han, K.-Z.; Guo, Q.-X. Synlett 2003, 870-872.
-
(2003)
Synlett
, pp. 870-872
-
-
Xue, S.1
Han, K.-Z.2
Guo, Q.-X.3
-
63
-
-
0037017749
-
-
Use of organoaluminum and organoboron reagents, see: Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997-2009.
-
(2002)
Tetrahedron
, vol.58
, pp. 1997-2009
-
-
Allwein, S.P.1
Cox, J.M.2
Howard, B.E.3
Johnson, H.W.B.4
Rainier, J.D.5
-
65
-
-
4043162596
-
-
4 semipinacol-type rearrangement of 2-cycloalkanol-substituted N-tosyl-1,4,5,6-tetrahydropyridines, see: Dake, G. R.; Fenster, M. D. B.; Fleury, M.; Patrick, B. O. J. Org. Chem. 2004, 69, 5676-5683.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 5676-5683
-
-
Dake, G.R.1
Fenster, M.D.B.2
Fleury, M.3
Patrick, B.O.4
-
66
-
-
77956698429
-
-
Isolation: (a) Ahmad, V. U.; Basha, A.; Haque, W. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1978, 33B, 347-348.
-
(1978)
Naturforsch., B: Anorg. Chem., Org. Chem.
, vol.33 B
, pp. 347-348
-
-
Ahmad, V.U.1
Basha, A.2
Haque, W.Z.3
-
67
-
-
0018639926
-
-
(b) Ahmad, V. U.; Usmanghani, K.; Najmus-Saqib, Q. Sci. Pharm. 1979, 47, 333-334.
-
(1979)
Sci. Pharm.
, vol.47
, pp. 333-334
-
-
Ahmad, V.U.1
Usmanghani, K.2
Najmus-Saqib, Q.3
-
68
-
-
29844438873
-
-
Absolute configuration determination: (c) Ahmad, V. U.; Qazi, S. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1983, 38B, 347-348.
-
(1983)
Naturforsch., B: Anorg. Chem., Org. Chem.
, vol.38 B
, pp. 347-348
-
-
Ahmad, V.U.1
Qazi, S.Z.2
-
69
-
-
0010314718
-
-
see ref 4r
-
For asymmetric synthesis of 1, see ref 4r. For racemic synthesis, see: Paterne, M.; Brown, É. C. R. Séances Acad. Sci., Ser. 2 1983, 296, 433-434.
-
(1983)
C. R. Séances Acad. Sci., Ser. 2
, vol.296
, pp. 433-434
-
-
Paterne, M.1
Brown, É.2
|