-
1
-
-
0037434512
-
-
For some selected reviews on the chemistry and biology of epibatidine and analogues, see: a
-
For some selected reviews on the chemistry and biology of epibatidine and analogues, see: (a) Daly, J. W. J. Med. Chem. 2003, 46, 445.
-
(2003)
J. Med. Chem
, vol.46
, pp. 445
-
-
Daly, J.W.1
-
4
-
-
0026551490
-
-
Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
-
(1992)
J. Am. Chem. Soc
, vol.114
, pp. 3475
-
-
Spande, T.F.1
Garraffo, H.M.2
Edwards, M.W.3
Yeh, H.J.C.4
Pannell, L.5
Daly, J.W.6
-
5
-
-
0031450275
-
-
Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169.
-
(1997)
J. Med. Chem
, vol.40
, pp. 4169
-
-
Holladay, M.W.1
Dart, M.J.2
Lynch, J.K.3
-
7
-
-
35948992185
-
-
(a) Gómez-Sánchez, E.; Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2007, 72, 8656
-
(2007)
J. Org. Chem
, vol.72
, pp. 8656
-
-
Gómez-Sánchez, E.1
Soriano, E.2
Marco-Contelles, J.3
-
8
-
-
37049100053
-
-
See also: b
-
See also: (b) Bastable, J. W.; Cooper, A. J.; Dunkin, I. R.; Hobson, J. D.; Riddell, W. D. J. Chem. Soc, Perkin Trans 1 1981, 1339.
-
(1981)
J. Chem. Soc, Perkin Trans 1
, pp. 1339
-
-
Bastable, J.W.1
Cooper, A.J.2
Dunkin, I.R.3
Hobson, J.D.4
Riddell, W.D.5
-
12
-
-
0031739373
-
-
(b) Seerden, J.-P. G.; Tulp, M. Th. M.; Scheeren, H. W.; Kruse, C. G. Bioorg. Med. Chem. 1998, 6, 2103.
-
(1998)
Bioorg. Med. Chem
, vol.6
, pp. 2103
-
-
Seerden, J.-P.G.1
Tulp, M.T.M.2
Scheeren, H.W.3
Kruse, C.G.4
-
13
-
-
51549109067
-
-
Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. US(1998)5817679.
-
(a) Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. US(1998)5817679.
-
-
-
-
14
-
-
51549099517
-
-
Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. WO1996 9606093.
-
(b) Shen, T. Y.; Harman, W. D.; Huang, D. F.; González, J. WO(1996 9606093.
-
-
-
-
20
-
-
0030788184
-
-
(b) Srikrishna, A.; Viswajanani, R.; Reddy, T. J.; Vijaykumar, D.; Kumar, P. P. J. Org. Chem. 1997, 62, 5232.
-
(1997)
J. Org. Chem
, vol.62
, pp. 5232
-
-
Srikrishna, A.1
Viswajanani, R.2
Reddy, T.J.3
Vijaykumar, D.4
Kumar, P.P.5
-
21
-
-
33646874386
-
-
(c) Liaw, D.-J.; Huang, C.-C.; Ju, J.-Y. J. Polym. Sci., Part A 2006, 44, 3382.
-
(2006)
J. Polym. Sci., Part A
, vol.44
, pp. 3382
-
-
Liaw, D.-J.1
Huang, C.-C.2
Ju, J.-Y.3
-
22
-
-
0025265145
-
-
Boivin, J.; da Silva, E.; Ourisson, G.; Zard, S. Tetrahedron Lett. 1990, 31, 2501.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 2501
-
-
Boivin, J.1
da Silva, E.2
Ourisson, G.3
Zard, S.4
-
23
-
-
0000913132
-
-
(b) Takasu, K.; Mizutani, S.; Nogushi, M.; Makita, K.; Ihara, M. Org. Lett. 1999, 1, 391.
-
(1999)
Org. Lett
, vol.1
, pp. 391
-
-
Takasu, K.1
Mizutani, S.2
Nogushi, M.3
Makita, K.4
Ihara, M.5
-
25
-
-
51549101539
-
-
-1) shows that this process appears to be clearly unfavored and hardly achievable in the reaction conditions.
-
-1) shows that this process appears to be clearly unfavored and hardly achievable in the reaction conditions.
-
-
-
-
26
-
-
35348842063
-
-
Armstrong, A.; Bhonoah, Y.; Shanahan, S. E. J. Org. Chem. 2007, 72, 8019.
-
(2007)
J. Org. Chem
, vol.72
, pp. 8019
-
-
Armstrong, A.1
Bhonoah, Y.2
Shanahan, S.E.3
-
28
-
-
51549086857
-
-
1N MR as the major product.
-
1N MR as the major product.
-
-
-
-
29
-
-
51549106810
-
-
Reference deleted in proof
-
Reference deleted in proof.
-
-
-
-
31
-
-
0001250488
-
-
(a) Duncia, J. V.; Pierce, M. E.; Santela, J. B., III J. Org. Chem. 1991, 56, 2395.
-
(1991)
J. Org. Chem
, vol.56
, pp. 2395
-
-
Duncia, J.V.1
Pierce, M.E.2
Santela III, J.B.3
-
33
-
-
0041519440
-
-
(c) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. 2003, 125, 9983.
-
(2003)
J. Am. Chem
, vol.125
, pp. 9983
-
-
Himo, F.1
Demko, Z.P.2
Noodleman, L.3
Sharpless, K.B.4
-
34
-
-
1842688821
-
-
(d) Amantini, D.; Beleggia, R.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2004, 69, 2896.
-
(2004)
J. Org. Chem
, vol.69
, pp. 2896
-
-
Amantini, D.1
Beleggia, R.2
Fringuelli, F.3
Pizzo, F.4
Vaccaro, L.5
-
35
-
-
27944492386
-
-
3, the reaction was incomplete and the yield of compound 7 was 12% (28%)].
-
3, the reaction was incomplete and the yield of compound 7 was 12% (28%)].
-
-
-
-
38
-
-
51549085370
-
-
C-Br that reduces the interaction energy in the transition state.
-
C-Br that reduces the interaction energy in the transition state.
-
-
-
-
39
-
-
0028968395
-
-
González, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 3405
-
-
González, J.1
Koontz, J.I.2
Hodges, L.M.3
Nilsson, K.R.4
Neely, L.K.5
Myers, W.H.6
Sabat, M.7
Harman, W.D.8
-
40
-
-
0032546068
-
-
Ohwada, T.; Achiwa, T.; Okamoto, I.; Shudo, K. Tetrahedron Lett. 1998, 39, 865.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 865
-
-
Ohwada, T.1
Achiwa, T.2
Okamoto, I.3
Shudo, K.4
-
41
-
-
51549087054
-
-
See Supporting Information for etails
-
See Supporting Information for etails.
-
-
-
-
42
-
-
0344236075
-
-
Otani, Y.; Nagae, O.; Naruse, Y.; Inagaki, S.; Ohno, M.; Yamaguchi, K.; Yamamoto, G.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2003, 125, 15191.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 15191
-
-
Otani, Y.1
Nagae, O.2
Naruse, Y.3
Inagaki, S.4
Ohno, M.5
Yamaguchi, K.6
Yamamoto, G.7
Uchiyama, M.8
Ohwada, T.9
-
48
-
-
27444433842
-
-
Kawamura, T.; Koyama, T.; Yonezawa, T. J. Am. Chem. Soc. 1973, 95, 3220.
-
(1973)
J. Am. Chem. Soc
, vol.95
, pp. 3220
-
-
Kawamura, T.1
Koyama, T.2
Yonezawa, T.3
-
49
-
-
0000638821
-
-
(a) Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974.
-
(1982)
J. Am. Chem. Soc
, vol.104
, pp. 4974
-
-
Rondan, N.G.1
Paddon-Row, M.N.2
Caramella, P.3
Mareda, J.4
Mueller, P.H.5
Houk, K.N.6
-
50
-
-
0020821964
-
-
(b) Houk, K. N.; Rondan, N. G.; Brown, F. K.; Jorgensen, W. L.; Madura, J. D.; Spellmeyer, D. C. J. Am. Chem. Soc. 1983, 105, 5980.
-
(1983)
J. Am. Chem. Soc
, vol.105
, pp. 5980
-
-
Houk, K.N.1
Rondan, N.G.2
Brown, F.K.3
Jorgensen, W.L.4
Madura, J.D.5
Spellmeyer, D.C.6
-
51
-
-
51549093289
-
-
A pioneering work by Schleyer focused attention on the relief of torsional strain involving the bridgehead CH bond in norbornyl systems and noted the general role of the transition-state torsional interactions: Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701
-
A pioneering work by Schleyer focused attention on the relief of torsional strain involving the bridgehead CH bond in norbornyl systems and noted the general role of the transition-state torsional interactions: Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701.
-
-
-
-
52
-
-
33947294739
-
-
For other works on the torsional effect, see: a
-
For other works on the "torsional effect", see: (a) Bartlett, P. D.; Fickes, G. N.; Haupt, F. C.; Helgeson, R. Acc. Chem. Res. 1970, 3, 177.
-
(1970)
Acc. Chem. Res
, vol.3
, pp. 177
-
-
Bartlett, P.D.1
Fickes, G.N.2
Haupt, F.C.3
Helgeson, R.4
-
53
-
-
0000623923
-
-
(b) Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. J. Am. Chem. Soc. 1980, 102, 3951.
-
(1980)
J. Am. Chem. Soc
, vol.102
, pp. 3951
-
-
Huisgen, R.1
Ooms, P.H.J.2
Mingin, M.3
Allinger, N.L.4
-
54
-
-
0001048498
-
-
(c) Watson, W. H.; Galloy, J.; Bartlett, P. D.; Roof, A. A. M. J. Am. Chem. Soc. 1981, 103, 2022.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 2022
-
-
Watson, W.H.1
Galloy, J.2
Bartlett, P.D.3
Roof, A.A.M.4
-
58
-
-
0033056473
-
-
(a) Ellis, J. L.; Harman, D.; González, J.; Spera, M. L.; Liu, R.; Shen, T. Y.; Wypij, D. M.; Zuo, F. J. Pharmacol. Exp. Ther. 1999, 288, 1143.
-
(1999)
J. Pharmacol. Exp. Ther
, vol.288
, pp. 1143
-
-
Ellis, J.L.1
Harman, D.2
González, J.3
Spera, M.L.4
Liu, R.5
Shen, T.Y.6
Wypij, D.M.7
Zuo, F.8
-
59
-
-
0036841143
-
-
(b) Duttaroy, A.; Gomeza, J.; Gan, J.-W.; Siddiqui, N.; Basile, A. S.; Harman, W. D.; Smith, P. L.; Felder, C. C.; Levey, A. I.; Wess, J. Mol. Pharmacol. 2002, 62, 1084.
-
(2002)
Mol. Pharmacol
, vol.62
, pp. 1084
-
-
Duttaroy, A.1
Gomeza, J.2
Gan, J.-W.3
Siddiqui, N.4
Basile, A.S.5
Harman, W.D.6
Smith, P.L.7
Felder, C.C.8
Levey, A.I.9
Wess, J.10
-
60
-
-
84979270321
-
-
Giese, B.; González-Gómez, J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69.
-
(1984)
Angew. Chem., Int. Ed. Engl
, vol.23
, pp. 69
-
-
Giese, B.1
González-Gómez, J.A.2
Witzel, T.3
-
61
-
-
51549099922
-
-
We have also investigated the free radical allylation34 of bromide 1, a reaction that provided the expected 1-(2-allyl-7- azabicyclo[2.2.1]heptan-7-yl)-2,2,2-trifluoroethanone (16) in an incomplete and low yielding reaction see Supporting Information Available
-
34 of bromide 1, a reaction that provided the expected 1-(2-allyl-7- azabicyclo[2.2.1]heptan-7-yl)-2,2,2-trifluoroethanone (16) in an incomplete and low yielding reaction (see Supporting Information Available).
-
-
-
-
63
-
-
0141704726
-
-
Frisch, M. J. et al. Gaussian, Inc, Wallingford, CT
-
Gaussian 03, Revision B.03; Frisch, M. J. et al. Gaussian, Inc.: Wallingford, CT, 2003.
-
(2003)
Gaussian 03, Revision B.03
-
-
-
64
-
-
0345491105
-
-
(a) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785-789
-
-
Lee, C.1
Yang, W.2
Parr, R.3
-
68
-
-
84962349001
-
-
(b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
-
(2003)
J. Comput. Chem
, vol.24
, pp. 669
-
-
Cossi, M.1
Rega, N.2
Scalmani, G.3
Barone, V.4
-
70
-
-
0011083499
-
-
(b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
-
(1988)
Chem. Rev
, vol.88
, pp. 899
-
-
Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
|