-
1
-
-
33751573921
-
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products
-
Padwa, A., Pearson, W. H., Eds.; Wiley: Chichester
-
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Chemistry of Heterocyclic Compounds Series 59; Wiley: Chichester, 2002.
-
(2002)
Chemistry of Heterocyclic Compounds Series 59
-
-
-
4
-
-
33645410218
-
Azomethine Imines
-
Georg Thieme Verlag: Stuttgart
-
(a) Schantl, J. G. Azomethine Imines. Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2004; Vol. 27, pp 731-824.
-
(2004)
Science of Synthesis
, vol.27
, pp. 731-824
-
-
Schantl, J.G.1
-
5
-
-
0000629986
-
Intermolecular 1.3-Dipolar Cycloadditions
-
Trost, B. M., Fleming, I., Eds.; Pergamon; London
-
(b) Padwa, A. Intermolecular 1.3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon; London, 1991; Vol. 4, pp 1069-1109.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1069-1109
-
-
Padwa, A.1
-
6
-
-
0000629986
-
Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations
-
Trost, B. M., Fleming, I., Eds.; Pergamon: London
-
(c) Wade, P. A. Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 4, pp 1144-49.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1144-1149
-
-
Wade, P.A.1
-
7
-
-
0021145635
-
-
(a) Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594-5598.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 5594-5598
-
-
Jacobi, P.A.1
Martinelli, M.J.2
Polanc, S.3
-
8
-
-
2142738586
-
-
(b) Jacobi, P. A.; Brownstein, A.; Martinelli, M.; Grozinger, K. J. Am. Chem. Soc. 1981, 103, 239-241.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 239-241
-
-
Jacobi, P.A.1
Brownstein, A.2
Martinelli, M.3
Grozinger, K.4
-
9
-
-
2142851503
-
-
(c) Martinelli, M. J.; Brownstein, A. D.; Jacobi, P. A.; Polanc, S. Croat. Chem. Acta 1986, 59, 267-295.
-
(1986)
Croat. Chem. Acta
, vol.59
, pp. 267-295
-
-
Martinelli, M.J.1
Brownstein, A.D.2
Jacobi, P.A.3
Polanc, S.4
-
10
-
-
0002527884
-
-
Grigg, R.; Kemp, J.; Thompson, N. Tetrahedron Lett. 1978, 31, 2827-2830.
-
(1978)
Tetrahedron Lett.
, vol.31
, pp. 2827-2830
-
-
Grigg, R.1
Kemp, J.2
Thompson, N.3
-
11
-
-
0039795046
-
-
Le Fevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821-1824.
-
(1979)
Tetrahedron
, vol.35
, pp. 1821-1824
-
-
Le Fevre, G.1
Sinbandhit, S.2
Hamelin, J.3
-
13
-
-
0036827533
-
-
For our earlier studies in this area, see: (a) Bélanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880-7883.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 7880-7883
-
-
Bélanger, G.1
Hong, F.-T.2
Overman, L.E.3
Rogers, B.N.4
Tellew, J.E.5
Trenkle, W.C.6
-
14
-
-
0030802072
-
-
(b) Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159-7160.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 7159-7160
-
-
Overman, L.E.1
Rogers, B.N.2
Tellew, J.E.3
Trenkle, W.C.4
-
15
-
-
0141518579
-
-
Nishimura, S.; Matsunaga, S.; Shibazaki, M.; Suzuki, K.; Furihata, K.; van Soest, R. W. M.; Fusetani, N. Org. Lett. 2003, 5, 2255-2257.
-
(2003)
Org. Lett.
, vol.5
, pp. 2255-2257
-
-
Nishimura, S.1
Matsunaga, S.2
Shibazaki, M.3
Suzuki, K.4
Furihata, K.5
Van Soest, R.W.M.6
Fusetani, N.7
-
20
-
-
0037134870
-
-
Scheidt, K. A.; Bannister, T. D.; Tasaka, A.; Wendt, M. D.; Savall, B. M.; Fegley, G. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 6981-6990.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 6981-6990
-
-
Scheidt, K.A.1
Bannister, T.D.2
Tasaka, A.3
Wendt, M.D.4
Savall, B.M.5
Fegley, G.J.6
Roush, W.R.7
-
21
-
-
0000476716
-
-
Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 2183-2186
-
-
Blanchette, M.A.1
Choy, W.2
Davis, J.T.3
Essenfeld, A.P.4
Masamune, S.5
Roush, W.R.6
Sakai, T.7
-
24
-
-
0000899124
-
-
(b) Horne, D.; Gaudino, J.; Thompson, W. J. Tetrahedron Lett. 1984, 25, 3529-3532.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 3529-3532
-
-
Horne, D.1
Gaudino, J.2
Thompson, W.J.3
-
25
-
-
33751559949
-
-
note
-
Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614479.
-
-
-
-
26
-
-
33751559239
-
-
note
-
Other solvents examined: toluene, 1,2-dichloroethane, acetic acid, acetonitrile, 2,2,2-trifluoroethanol, and N,N-dimethylformamide.
-
-
-
-
27
-
-
33751583402
-
-
note
-
Wittig reaction of aldehyde 8 with methoxymethyltriphenylphosphonium chloride and potassium hexamethyldisilazane (KHMDS) in THF, followed by hydrolysis of the resulting enol ether with aqueous hydrochloric acid in THF, gave aldehyde 48 in 85% yield over two steps.
-
-
-
-
28
-
-
33751565051
-
-
note
-
A Monte Carlo conformational search was performed using the MMFF force field as implemented in Spartan 2005.
-
-
-
-
29
-
-
33751568183
-
-
note
-
The cis cycloadduct 41 was calculated to have a conformational energy of 163.4 kcal/mol, whereas the cycloadduct (epimeric at C3 and C3a) had a conformational energy of 171.9 kcal/mol.
-
-
-
-
31
-
-
33751564892
-
-
note
-
Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614481.
-
-
-
-
32
-
-
33751561986
-
-
note
-
Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614480.
-
-
-
-
33
-
-
33751559077
-
-
note
-
The toluene/PPTS conditions were also examined with substrates that contained α-methoxy, α,β-unsaturated esters dipolarophile fragments. In these cases, the cycloaddition substrates decomposed to give intractable mixtures.
-
-
-
-
34
-
-
33751560693
-
-
note
-
Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614482.
-
-
-
-
36
-
-
1642345364
-
-
(b) Chung, F.; Chauveau, A.; Seltki, M.; Bonin, M.; Micouin, L. Tetrahedron Lett. 2004, 45, 3127-3130.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 3127-3130
-
-
Chung, F.1
Chauveau, A.2
Seltki, M.3
Bonin, M.4
Micouin, L.5
-
37
-
-
0037436907
-
-
(c) Kobayashi, S.; Hirabayashi, R.; Shimizu, H.; Ishitani, H.; Yamashita, Y. Tetrahedron Lett. 2003, 44, 3351-3354.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 3351-3354
-
-
Kobayashi, S.1
Hirabayashi, R.2
Shimizu, H.3
Ishitani, H.4
Yamashita, Y.5
-
38
-
-
0037146071
-
-
(d) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678-13679.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13678-13679
-
-
Kobayashi, S.1
Shimizu, H.2
Yamashita, Y.3
Ishitani, H.4
Kobayashi, J.5
-
42
-
-
0041931082
-
-
Lewis acids have also been used to promote related azomethine ylide cycloadditions: (a) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10174-10175
-
-
Chen, C.1
Li, X.2
Schreiber, S.L.3
-
43
-
-
0028828504
-
-
(b) Nyerges, M.; Rudas, M.; Toth, G.; Herenyi, B.; Kadas, I.; Bitter, I.; Toke, L. Tetrahedron 1995, 48, 13321-13330.
-
(1995)
Tetrahedron
, vol.48
, pp. 13321-13330
-
-
Nyerges, M.1
Rudas, M.2
Toth, G.3
Herenyi, B.4
Kadas, I.5
Bitter, I.6
Toke, L.7
-
44
-
-
0001186548
-
-
Carlson, R.; Lundstedt, A. N.; Prochazka, M. Acta Chem. Scand. 1986, 40B, 522-533.
-
(1986)
Acta Chem. Scand.
, vol.40 B
, pp. 522-533
-
-
Carlson, R.1
Lundstedt, A.N.2
Prochazka, M.3
-
45
-
-
33751570209
-
-
note
-
2.
-
-
-
-
46
-
-
29244479725
-
-
For a general review of microwave chemistry, see: Galema, S. A. Chem. Soc. Rev. 1997, 26, 233-238.
-
(1997)
Chem. Soc. Rev.
, vol.26
, pp. 233-238
-
-
Galema, S.A.1
-
47
-
-
0032558604
-
-
Microwave irradiation has previously been reported to promote intermolecular azomethine imine cycloaddition reactions, see: Arrieta, A.; Carrillo, J. R.; Cossío, F. P.; Díaz-Ortiz, A.; Gómez-Escalonilla, M. J.; de la Hoz, A.; Langa, F.; Moreno, A. Tetrahedron 1998, 54, 13167-13180.
-
(1998)
Tetrahedron
, vol.54
, pp. 13167-13180
-
-
Arrieta, A.1
Carrillo, J.R.2
Cossío, F.P.3
Díaz-Ortiz, A.4
Gómez-Escalonilla, M.J.5
De La Hoz, A.6
Langa, F.7
Moreno, A.8
-
49
-
-
33947085599
-
-
(a) Houk, K. N.; Sims, J.; Duke, R. E., Jr.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287-7301.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 7287-7301
-
-
Houk, K.N.1
Sims, J.2
Duke Jr., R.E.3
Strozier, R.W.4
George, J.K.5
-
50
-
-
17844396162
-
-
(b) Houk, K. N.; Sims, J.; Watts, C. R.; Kuskus, L. J. J. Am. Chem. Soc. 1973, 95, 7301-7315.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 7301-7315
-
-
Houk, K.N.1
Sims, J.2
Watts, C.R.3
Kuskus, L.J.4
-
51
-
-
0037377598
-
-
Although bicyclo[3.3.0]octane ring systems are generally observed in intermolecular dipolar cycloadditions in which a dipole is connected to an alkene through a three-carbon tether, bicyclo[3.2.1]octane ring systems have been observed, see: Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628.
-
(2003)
Curr. Org. Chem.
, vol.7
, pp. 585-628
-
-
Koumbis, A.E.1
Gallos, J.K.2
-
52
-
-
0035913709
-
-
All cycloaddition reactions were performed in thick-walled sealed tubes for reaction volumes greater than 2 mL and in screw-cap vials with Teflon caps for reaction volumes of 2 mL or less. Other general experimental details have been described: MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9033-9044
-
-
MacMillan, D.W.C.1
Overman, L.E.2
Pennington, L.D.3
|