-
1
-
-
0003916113
-
-
Padwa, A., Pearson, W. H., Eds.; John Wiley & Sons: New York
-
(a) Harwood, L. M.; Vickers, R. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002; pp 169-252.
-
(2002)
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products
, pp. 169-252
-
-
Harwood, L.M.1
Vickers, R.J.2
-
2
-
-
0002430420
-
-
Curran, D. P., Ed.; JAI Press: Greenwich CT
-
(b) Kanemasa, S.; Tsuge, O. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993; Vol. 3, pp 99-159.
-
(1993)
Advances in Cycloaddition
, vol.3
, pp. 99-159
-
-
Kanemasa, S.1
Tsuge, O.2
-
3
-
-
0004136903
-
-
Curran, D. P., Ed.; JAI Press: Greenwich CT
-
(c) Grigg, R.; Sridharan, V. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993; Vol. 3, pp 161-204.
-
(1993)
Advances in Cycloaddition
, vol.3
, pp. 161-204
-
-
Grigg, R.1
Sridharan, V.2
-
4
-
-
0000629986
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK
-
(d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, pp 1069-1109.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1069-1109
-
-
Padwa, A.1
-
5
-
-
0000629986
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK
-
(e) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, pp 1111-1168.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1111-1168
-
-
Wade, P.A.1
-
6
-
-
0003525808
-
-
Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands
-
(f) Pearson, W. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1988; Vol. 1, pp 323-358.
-
(1988)
Studies in Natural Products Chemistry
, vol.1
, pp. 323-358
-
-
Pearson, W.H.1
-
7
-
-
0002707988
-
-
Curran, D. P., Ed.; JAI Press: Greenwich, CT
-
(g) Vedejs, E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51.
-
(1988)
Advances in Cycloaddition
, vol.1
, pp. 33-51
-
-
Vedejs, E.1
-
8
-
-
0004101860
-
-
Padwa, A., Ed.; John Wiley & Sons: New York
-
(h) Lown, W. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp 653-733.
-
(1984)
1,3-Dipolar Cycloaddition Chemistry
, vol.1
, pp. 653-733
-
-
Lown, W.J.1
-
9
-
-
1642271643
-
-
Padwa, A., Ed.; John Wiley & Sons: New York
-
(i) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, pp 227-387.
-
(1984)
1,3-Dipolar Cycloaddition Chemistry
, vol.2
, pp. 227-387
-
-
Padwa, A.1
-
13
-
-
0001470638
-
-
(a) Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981-1008.
-
(1988)
Heterocycles
, vol.27
, pp. 981-1008
-
-
Terao, Y.1
Aono, M.2
Achiwa, K.3
-
14
-
-
85008538393
-
-
(b) Achiwa, K.; Motoyama, T.; Sekiya, M. Chem. Pharm. Bull. 1983, 31, 3939-3945.
-
(1983)
Chem. Pharm. Bull.
, vol.31
, pp. 3939-3945
-
-
Achiwa, K.1
Motoyama, T.2
Sekiya, M.3
-
18
-
-
0034084514
-
-
Obst, U.; Betschmann, P.; Lerner, C.; Seiler, P.; Diederich, F.; Gramlich, V.; Weber, L.; Banner, D. W.; Schonholzer, P. Helv. Chim. Acta 2000, 83, 855-909.
-
(2000)
Helv. Chim. Acta
, vol.83
, pp. 855-909
-
-
Obst, U.1
Betschmann, P.2
Lerner, C.3
Seiler, P.4
Diederich, F.5
Gramlich, V.6
Weber, L.7
Banner, D.W.8
Schonholzer, P.9
-
20
-
-
0001570148
-
-
Vedejs, E.; Larsen, S.; West, F. G. J. Org. Chem. 1985, 50, 2170-2174.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 2170-2174
-
-
Vedejs, E.1
Larsen, S.2
West, F.G.3
-
22
-
-
0036263857
-
-
Epperson, M. T.; Gin, D. Y. Angew. Chem., Int. Ed. 2002, 41, 1778-1780.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 1778-1780
-
-
Epperson, M.T.1
Gin, D.Y.2
-
23
-
-
0035944163
-
-
For pyrrolizidines or indolizidines made from nonstabilized azomethine ylides (i.e. bearing only hydrogens or alkyl groups) see: (a) Castulik, J.; Marek, J.; Mazal, C. Tetrahedron 2001, 57, 8339-8347.
-
(2001)
Tetrahedron
, vol.57
, pp. 8339-8347
-
-
Castulik, J.1
Marek, J.2
Mazal, C.3
-
24
-
-
0030740508
-
-
(b) Grigg, R.; Savic, V.; Thornton-Pett, M. Tetrahedron 1997, 53, 10633-10642.
-
(1997)
Tetrahedron
, vol.53
, pp. 10633-10642
-
-
Grigg, R.1
Savic, V.2
Thornton-Pett, M.3
-
25
-
-
0002002223
-
-
(c) Novello, F.; Prato, M.; Da Ros, T.; De Amici, M.; Bianco, A.; Toniolo, C.; Maggini, M. Chem. Commun. 1996, 903-904.
-
(1996)
Chem. Commun.
, pp. 903-904
-
-
Novello, F.1
Prato, M.2
Da Ros, T.3
De Amici, M.4
Bianco, A.5
Toniolo, C.6
Maggini, M.7
-
29
-
-
0000403545
-
-
(g) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079-4089.
-
(1987)
Bull. Chem. Soc. Jpn.
, vol.60
, pp. 4079-4089
-
-
Tsuge, O.1
Kanemasa, S.2
Ohe, M.3
Takenaka, S.4
-
31
-
-
0020366127
-
-
(i) Terao, Y.; Imai, N.; Achiwa, K.; Sekiya, M. Chem. Pharm. Bull. 1982, 30, 3167-3171.
-
(1982)
Chem. Pharm. Bull.
, vol.30
, pp. 3167-3171
-
-
Terao, Y.1
Imai, N.2
Achiwa, K.3
Sekiya, M.4
-
34
-
-
0034608088
-
-
(b) Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56, 2929-2934.
-
(2000)
Tetrahedron
, vol.56
, pp. 2929-2934
-
-
Morita, H.1
Arisaka, M.2
Yoshida, N.3
Kobayashi, J.4
-
35
-
-
0035010761
-
-
(c) Garraffo, H. M.; Jain, P.; Spande, T. F.; Daly, J. W.; Jones, T. H.; Smith, L. J.; Zottig, V. E. J. Nat. Prod. 2001, 64, 421-427.
-
(2001)
J. Nat. Prod.
, vol.64
, pp. 421-427
-
-
Garraffo, H.M.1
Jain, P.2
Spande, T.F.3
Daly, J.W.4
Jones, T.H.5
Smith, L.J.6
Zottig, V.E.7
-
38
-
-
0026536264
-
-
(b) Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329-1345.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 1329-1345
-
-
Pearson, W.H.1
Szura, D.P.2
Postich, M.J.3
-
41
-
-
0001543645
-
-
(a) Padwa, A.; Fryxell, A.; Gasdaska, J. R.; Venkatramanan, M. K. J. Org. Chem. 1989, 54, 644-653.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 644-653
-
-
Padwa, A.1
Fryxell, A.2
Gasdaska, J.R.3
Venkatramanan, M.K.4
-
42
-
-
0000267010
-
-
(b) Padwa, A.; Eisenbarth, P.; Venkatramanan, M. K.; Wong, G. S. K. J. Org. Chem. 1987, 52, 2427-2432.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 2427-2432
-
-
Padwa, A.1
Eisenbarth, P.2
Venkatramanan, M.K.3
Wong, G.S.K.4
-
43
-
-
0000293748
-
-
(c) Padwa, A.; Chen, Y.-Y.; Dent, W.; Nimmesgern, H. J. Org. Chem. 1985, 50, 4006-4014.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 4006-4014
-
-
Padwa, A.1
Chen, Y.-Y.2
Dent, W.3
Nimmesgern, H.4
-
44
-
-
0000387957
-
-
(d) Padwa, A.; Chen, Y.-Y.; Chiacchio, U.; Dent, W. Tetrahedron 1985, 41, 3529-3535.
-
(1985)
Tetrahedron
, vol.41
, pp. 3529-3535
-
-
Padwa, A.1
Chen, Y.-Y.2
Chiacchio, U.3
Dent, W.4
-
46
-
-
0037193107
-
-
and references therein
-
Pandey, G.; Laha, J. K.; Lakshmaiah, G. Tetrahedron 2002, 58, 3525-3534 and references therein.
-
(2002)
Tetrahedron
, vol.58
, pp. 3525-3534
-
-
Pandey, G.1
Laha, J.K.2
Lakshmaiah, G.3
-
50
-
-
0037915098
-
-
(b) Achiwa, K.; Imai, N.; Inaoka, T.; Sekiya, M. Chem. Pharm. Bull. 1984, 32, 2878-2881.
-
(1984)
Chem. Pharm. Bull.
, vol.32
, pp. 2878-2881
-
-
Achiwa, K.1
Imai, N.2
Inaoka, T.3
Sekiya, M.4
-
52
-
-
0042566349
-
-
Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435-438.
-
(2003)
Org. Lett.
, vol.5
, pp. 435-438
-
-
Bora, U.1
Saikia, A.2
Boruah, R.C.3
-
53
-
-
0141519434
-
-
Li, G.-Y.; Chen, J.; Yu, W.-Y.; Hong, W.; Che, C.-M. Org. Lett. 2003, 5, 2153-2156.
-
(2003)
Org. Lett.
, vol.5
, pp. 2153-2156
-
-
Li, G.-Y.1
Chen, J.2
Yu, W.-Y.3
Hong, W.4
Che, C.-M.5
-
54
-
-
0344392778
-
-
Galliford, C. V.; Beenen, M. A.; Nguyen, S. T.; Scheidt, K. A. Org. Lett. 2003, 5, 3487-3490.
-
(2003)
Org. Lett.
, vol.5
, pp. 3487-3490
-
-
Galliford, C.V.1
Beenen, M.A.2
Nguyen, S.T.3
Scheidt, K.A.4
-
55
-
-
2542509173
-
-
For reviews see: (a) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 3168-3210
-
-
Domling, A.1
Ugi, I.2
-
56
-
-
0000512227
-
-
(b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
-
(1996)
Acc. Chem. Res.
, vol.29
, pp. 123-131
-
-
Armstrong, R.W.1
Combs, A.P.2
Tempest, P.A.3
Brown, S.D.4
Keating, T.A.5
-
61
-
-
85081429450
-
-
note
-
See the Supporting Information for an improved procedure for the preparation of 9.
-
-
-
-
62
-
-
0000548131
-
-
(a) Tsuge, O.; Kanemasa, S.; Yamada, T.; Matsuda, K. J. Org. Chem. 1987, 52, 2523-2530.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 2523-2530
-
-
Tsuge, O.1
Kanemasa, S.2
Yamada, T.3
Matsuda, K.4
-
63
-
-
0001574314
-
-
(b) Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Bull. Chem. Soc. Jpn. 1986, 59, 2537-2545.
-
(1986)
Bull. Chem. Soc. Jpn.
, vol.59
, pp. 2537-2545
-
-
Tsuge, O.1
Kanemasa, S.2
Hatada, A.3
Matsuda, K.4
-
64
-
-
0001127294
-
-
(c) Tsuge, O.; Kanemasa, S.; Yamada, T.; Matsuda, K. Heterocycles 1985, 23, 2489-2492.
-
(1985)
Heterocycles
, vol.23
, pp. 2489-2492
-
-
Tsuge, O.1
Kanemasa, S.2
Yamada, T.3
Matsuda, K.4
-
65
-
-
0002624549
-
-
(d) Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Chem. Lett. 1984, 801-804.
-
(1984)
Chem. Lett.
, pp. 801-804
-
-
Tsuge, O.1
Kanemasa, S.2
Hatada, A.3
Matsuda, K.4
-
67
-
-
0013567131
-
-
(a) Grigg, R.; Surendrakumar, S.; Thianpatanagul, S.; Vipond, D. J. Chem. Soc., Chem. Commun. 1987, 47-49.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 47-49
-
-
Grigg, R.1
Surendrakumar, S.2
Thianpatanagul, S.3
Vipond, D.4
-
68
-
-
12644310865
-
-
(b) Grigg, R.; Idle, J.; McMeekin, P.; Vipond, D. J. Chem. Soc., Chem. Commun. 1987, 49-51.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 49-51
-
-
Grigg, R.1
Idle, J.2
McMeekin, P.3
Vipond, D.4
-
69
-
-
0000403545
-
-
(c) Tsuge, O.; Kanemasa, S.; Masayuki, O.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079-4089.
-
(1987)
Bull. Chem. Soc. Jpn.
, vol.60
, pp. 4079-4089
-
-
Tsuge, O.1
Kanemasa, S.2
Masayuki, O.3
Takenaka, S.4
-
70
-
-
85081427526
-
-
note
-
In the generation of nonstabilized azomethine ylides by fluoride-induced desilylation of N-(trimethylsilyl)methyl iminium salts, the added fluoride source typically must be anhydrous. See refs 1d and 2.
-
-
-
-
71
-
-
0035922327
-
-
Savall, B.; Powell, N. A.; Roush, W. R. Org. Lett. 2001, 3, 3057-3060.
-
(2001)
Org. Lett.
, vol.3
, pp. 3057-3060
-
-
Savall, B.1
Powell, N.A.2
Roush, W.R.3
-
73
-
-
1642344812
-
-
(b) Clemens, M.; Meise, W.; Himmel, K.; Jansen, M. Liebigs Ann. Org. Bioorg. Chem. 1997, 2, 447-457.
-
(1997)
Liebigs Ann. Org. Bioorg. Chem.
, vol.2
, pp. 447-457
-
-
Clemens, M.1
Meise, W.2
Himmel, K.3
Jansen, M.4
-
74
-
-
1642323774
-
-
(c) Meise, W.; Arth, C.; Zlotos, D.; Jansen, M.; Feldmann, C. Liebigs Ann. Org. Bioorg. Chem. 1994, 1135-1142.
-
(1994)
Liebigs Ann. Org. Bioorg. Chem.
, pp. 1135-1142
-
-
Meise, W.1
Arth, C.2
Zlotos, D.3
Jansen, M.4
Feldmann, C.5
-
77
-
-
0037162667
-
-
Coldham, I.; Crapnell, K. M.; Fernandez, J.-C.; Moseley, J. D.; Rabot, R. J. Org. Chem. 2002, 67, 6181-6187.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 6181-6187
-
-
Coldham, I.1
Crapnell, K.M.2
Fernandez, J.-C.3
Moseley, J.D.4
Rabot, R.5
-
78
-
-
0012789384
-
-
(a) Fishwick, C. W. G.; Jones, A. D.; Mitchell, M. B. Tetrahedron Lett. 1989, 30, 4447-4448.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 4447-4448
-
-
Fishwick, C.W.G.1
Jones, A.D.2
Mitchell, M.B.3
-
81
-
-
0001726634
-
-
Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554-1555 and refs 29a, 29c, and 37c. Many other reports of water or halide as desilylating agents for N-(trimethylsilyl)methyl iminiums conspicuously lack enolizable hydrogens. For example see refs 4b, 4c, 20a, 20b, 29b, and 29d.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 1554-1555
-
-
Smith, R.1
Livinghouse, T.2
-
84
-
-
0032516288
-
-
Hon, Y.-S.; Chang, F.-J.; Lu, L.; Lin, W.-C. Tetrahedron 1998, 54, 5233-5246.
-
(1998)
Tetrahedron
, vol.54
, pp. 5233-5246
-
-
Hon, Y.-S.1
Chang, F.-J.2
Lu, L.3
Lin, W.-C.4
-
85
-
-
37049089628
-
-
Kurita, J.; Ishii, M.; Yasuike, S.; Tsuchiya, T. J. Chem. Soc., Chem. Commun. 1993, 17, 1309-1310.
-
(1993)
J. Chem. Soc., Chem. Commun.
, vol.17
, pp. 1309-1310
-
-
Kurita, J.1
Ishii, M.2
Yasuike, S.3
Tsuchiya, T.4
-
86
-
-
37049073662
-
-
Takahata, H.; Takahashi, K.; Wang, E. C.; Yamazaki, T. J. Chem. Soc., Perkin Trans. 1 1989, 1211-1214.
-
(1989)
J. Chem. Soc., Perkin Trans. 1
, pp. 1211-1214
-
-
Takahata, H.1
Takahashi, K.2
Wang, E.C.3
Yamazaki, T.4
-
88
-
-
0037009990
-
-
For a recent example see: Kusama, H.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 11592-11593.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11592-11593
-
-
Kusama, H.1
Takaya, J.2
Iwasawa, N.3
-
89
-
-
0037421133
-
-
(a) Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. Tetrahedron 2003, 59, 197-205.
-
(2003)
Tetrahedron
, vol.59
, pp. 197-205
-
-
Okada, H.1
Akaki, T.2
Oderaotoshi, Y.3
Minakata, S.4
Komatsu, M.5
-
90
-
-
0000475163
-
-
(b) Komatsu, M.; Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S. Org. Lett. 2002, 4, 3505-3508.
-
(2002)
Org. Lett.
, vol.4
, pp. 3505-3508
-
-
Komatsu, M.1
Okada, H.2
Akaki, T.3
Oderaotoshi, Y.4
Minakata, S.5
-
91
-
-
0001442914
-
-
(c) Komatsu, M.; Ohno, M.; Tsuno, S.; Ohshiro, Y. Chem. Lett. 1990, 575-576.
-
(1990)
Chem. Lett.
, pp. 575-576
-
-
Komatsu, M.1
Ohno, M.2
Tsuno, S.3
Ohshiro, Y.4
-
93
-
-
0037450461
-
-
Also see ref 46a
-
Komatsu, M.; Okada, H.; Yokoi, S.; Minakata, S. Tetrahedron Lett. 2003, 44, 1603-1606. Also see ref 46a.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 1603-1606
-
-
Komatsu, M.1
Okada, H.2
Yokoi, S.3
Minakata, S.4
-
94
-
-
85081429073
-
-
note
-
Interestingly, Torii (ref 30) reports a successful azomethine ylide cycloaddition involving the condensation of isobutyraldehyde with N-(trimethylsilylmethyl)benzylamine in THF, which presumably proceeds through iminium 51 in Scheme 12. In Torii's case, water or hydroxide are the likely desilylating agents, as opposed to chloride or bromide in our case.
-
-
-
-
100
-
-
0000602888
-
-
(b) Lambert, J. B.; Wang, G.-T.; Teramura, D. H. J. Org. Chem. 1988, 53, 5422-5428.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 5422-5428
-
-
Lambert, J.B.1
Wang, G.-T.2
Teramura, D.H.3
|