-
1
-
-
0000179903
-
-
Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
-
(1990)
Chem. Ber.
, vol.123
, pp. 2039
-
-
Brehme, R.1
-
2
-
-
0000082761
-
-
Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 1131
-
-
Brehme, R.1
Nikolajewski, H.E.2
-
3
-
-
0001167637
-
-
Brehme, R. Chem. Ber. 1990, 123, 2039. Brehme, R.; Nikolajewski, H. E. Tetrahedron Lett. 1982, 23, 1131. Brehme, R.; Nikolajewski, H. E. Tetrahedron 1976, 32, 731.
-
(1976)
Tetrahedron
, vol.32
, pp. 731
-
-
Brehme, R.1
Nikolajewski, H.E.2
-
4
-
-
0000272625
-
-
Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokohama, T. J. Org. Chem. 1988, 53, 129. Kamitori, Y.; Hojo, M.; Masuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 129
-
-
Kamitori, Y.1
Hojo, M.2
Masuda, R.3
Fujitani, T.4
Ohara, S.5
Yokohama, T.6
-
5
-
-
0001536457
-
-
Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokohama, T. J. Org. Chem. 1988, 53, 129. Kamitori, Y.; Hojo, M.; Masuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 519
-
-
Kamitori, Y.1
Hojo, M.2
Masuda, R.3
Yoshida, T.4
Ohara, S.5
Yamada, K.6
Yoshikawa, N.7
-
7
-
-
0030184490
-
-
(b) Lassaletta, J. M.; Fernández, R.; Gasch, C.; Vázquez, J. Tetrahedron 1996, 52, 9143.
-
(1996)
Tetrahedron
, vol.52
, pp. 9143
-
-
Lassaletta, J.M.1
Fernández, R.2
Gasch, C.3
Vázquez, J.4
-
8
-
-
0029899642
-
-
(c) Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M. Synthesis 1996, 627.
-
(1996)
Synthesis
, pp. 627
-
-
Fernández, R.1
Gasch, C.2
Lassaletta, J.M.3
Llera, J.M.4
-
9
-
-
0030068354
-
-
(d) Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M. Synthesis 1996, 48.
-
(1996)
Synthesis
, pp. 48
-
-
Enders, D.1
Syrig, R.2
Raabe, G.3
Fernández, R.4
Gasch, C.5
Lassaletta, J.M.6
Llera, J.M.7
-
10
-
-
0030570887
-
-
Lassaletta, J. M.; Fernández, R.; Martín-Zamora, E.; Pareja, C. Tetrahedron Lett. 1996, 37, 5787.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 5787
-
-
Lassaletta, J.M.1
Fernández, R.2
Martín-Zamora, E.3
Pareja, C.4
-
11
-
-
0029931674
-
-
(a) Lassaletta, J. M.; Fernandez, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 7002
-
-
Lassaletta, J.M.1
Fernandez, R.2
Martín-Zamora, E.3
Díez, E.4
-
12
-
-
0030790372
-
-
(b) Díez, E.; Fernández, F.; Gash, C.; Lassaletta, J. M.; Llera, J. M.; Martín-Zamora, E.; Vázquez, J. J. Org. Chem. 1997, 62, 2, 5144.
-
(1997)
J. Org. Chem.
, vol.62
, Issue.2
, pp. 5144
-
-
Díez, E.1
Fernández, F.2
Gash, C.3
Lassaletta, J.M.4
Llera, J.M.5
Martín-Zamora, E.6
Vázquez, J.7
-
13
-
-
0142038680
-
-
Fernández, R.; Martín-Zamora, E.; Pareja, C.; Vázquez, J.; Díez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1985, 24, 349.
-
(1985)
Angew. Chem., Int. Ed. Engl.
, vol.24
, pp. 349
-
-
Fernández, R.1
Martín-Zamora, E.2
Pareja, C.3
Vázquez, J.4
Díez, E.5
Monge, A.6
Lassaletta, J.M.7
-
14
-
-
0000716787
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., Chapter 1.12
-
Volkmann A. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 1, Chapter 1.12.
-
(1991)
Comprehensive Organic Synthesis
, vol.1
-
-
Volkmann, A.V.1
-
15
-
-
0027535784
-
-
Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M.; Vázquez, J. Tetrahedron Lett. 1993, 34, 141.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 141
-
-
Fernández, R.1
Gasch, C.2
Lassaletta, J.M.3
Llera, J.M.4
Vázquez, J.5
-
16
-
-
0030068354
-
-
(a) Preparation: Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Liera, J. M. Synthesis 1996, 48.
-
(1996)
Synthesis
, pp. 48
-
-
Enders, D.1
Syrig, R.2
Raabe, G.3
Fernández, R.4
Gasch, C.5
Lassaletta, J.M.6
Liera, J.M.7
-
17
-
-
0002434332
-
-
(b) For a review on the use of formaldehyde SAMP-hydrazone as chiral, neutral formylating reagent see: Enders, D.; Bolkenius, M.; Vázquez, J.; Lassaletta, J. M.; Fernández, R. J. Prakt. Chem. 1998, 340, 281.
-
(1998)
J. Prakt. Chem.
, vol.340
, pp. 281
-
-
Enders, D.1
Bolkenius, M.2
Vázquez, J.3
Lassaletta, J.M.4
Fernández, R.5
-
18
-
-
0030924784
-
-
For a recent, comprehensive review on asymmetric addition of organometallics to the CN double bond of hydrazones see: Enders, D.; Reinhold, U. Tetrahedron Asymmetry 1997, 8, 1895.
-
(1997)
Tetrahedron Asymmetry
, vol.8
, pp. 1895
-
-
Enders, D.1
Reinhold, U.2
-
19
-
-
0001448995
-
-
( 11) Very recently, Kobayashi et al. have reported on the rare earth triflate-catalyzed addition of silyl enolates to monoacylhydrazones: (a) Oyamada, H.; Kobayashi, S. Synlett 1998, 249.
-
(1998)
Synlett
, pp. 249
-
-
Oyamada, H.1
Kobayashi, S.2
-
20
-
-
0000290208
-
-
(b) Kobayashi, S.; Furuta, T.; Sugita, K.; Oyamada, H. Synlett 1998, 1019. The addition of these weaker nucleophiles, however, appears to be restricted to activated hydrazones.
-
(1998)
Synlett
, vol.1019
-
-
Kobayashi, S.1
Furuta, T.2
Sugita, K.3
Oyamada, H.4
-
21
-
-
37049097940
-
-
(a) Takahashi, H.; Tomita, K.; Otomasu, H. J. Chem. Soc., Chem. Commun. 1979, 668.
-
(1979)
J. Chem. Soc., Chem. Commun.
, pp. 668
-
-
Takahashi, H.1
Tomita, K.2
Otomasu, H.3
-
22
-
-
0022838866
-
-
(b) Claremon, D. A.; Lumma, P. K.; Phillips, B. T. J. Am. Chem. Soc. 1986, 108, 8265.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 8265
-
-
Claremon, D.A.1
Lumma, P.K.2
Phillips, B.T.3
-
24
-
-
0029117516
-
-
(d) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Manganey, P.; Feneau-Dupont, J.; Declercq, J. P. Synthesis 1995, 1038.
-
(1995)
Synthesis
, pp. 1038
-
-
Alexakis, A.1
Lensen, N.2
Tranchier, J.-P.3
Manganey, P.4
Feneau-Dupont, J.5
Declercq, J.P.6
-
26
-
-
0032546885
-
-
(f) Bataille, P.; Paterne, M.; Brown, E. Tetrahedron Asymmetry 1998, 9, 2181.
-
(1998)
Tetrahedron Asymmetry
, vol.9
, pp. 2181
-
-
Bataille, P.1
Paterne, M.2
Brown, E.3
-
27
-
-
0000556677
-
-
(g) Hsieh, Y.-T.; Lee, G.-H.; Wang, Y.; Luh, T.-Y. J. Org. Chem. 1998, 63, 1484.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 1484
-
-
Hsieh, Y.-T.1
Lee, G.-H.2
Wang, Y.3
Luh, T.-Y.4
-
28
-
-
84985624865
-
-
(a) Enders, D.; Nübling, C.; Schubert, H. Angew. Chem., Int. Ed. Engl. 1986, 25, 1109.
-
(1986)
Angew. Chem., Int. Ed. Engl.
, vol.25
, pp. 1109
-
-
Enders, D.1
Nübling, C.2
Schubert, H.3
-
31
-
-
0000889671
-
-
(a) Imamoto, T.; Sugiura, Y.; Takiyama, N.; Tetrahedron Lett. 1984, 25, 4233.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 4233
-
-
-
32
-
-
33845471319
-
-
(b) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 3904
-
-
Imamoto, T.1
Kusumoto, T.2
Tawarayama, Y.3
Sugiura, Y.4
Mita, T.5
Hatanaka, Y.6
Yokoyama, M.7
-
35
-
-
0032558659
-
-
The scope and limitations of the direct thioketalation of hydrazones has been investigated: Díez, E.; López, A. M.; Pareja, C.; Martín-Zamora, E.; Fernández, R.; Lassaletta, J. M. Tetrahedron Lett. 1998, 39, 7955.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 7955
-
-
Díez, E.1
López, A.M.2
Pareja, C.3
Martín-Zamora, E.4
Fernández, R.5
Lassaletta, J.M.6
-
36
-
-
0345034044
-
-
note
-
It should be noted that the steric differences between the "small" (methyl) and "medium" (methylene in the ring) substituents in these cases are clearly less than for the tertiary compound.
-
-
-
-
37
-
-
0000642086
-
-
and references therein
-
Organocerium compounds are claimed to possess better nucleophilicity and less basic character than organolithium or Grignard reagents: Denmark, S. E.; Edwards, J. P.; Nicaise, O. J. Org. Chem. 1993, 58, 8, 569 and references therein.
-
(1993)
J. Org. Chem.
, vol.58
, Issue.8
, pp. 569
-
-
Denmark, S.E.1
Edwards, J.P.2
Nicaise, O.3
-
38
-
-
0001649560
-
-
Denmark, S. E.; Nicaise, O.; Edwards, J. P. J. Org. Chem. 1990, 55, 5, 6219.
-
(1990)
J. Org. Chem.
, vol.55
, Issue.5
, pp. 6219
-
-
Denmark, S.E.1
Nicaise, O.2
Edwards, J.P.3
-
39
-
-
0344603117
-
-
note
-
It is important to wash the catalyst repeatedly with water to neutrality and then with methanol prior to use. Direct washing of the catalyst with methanol resulted in the unexpected N-methylation of the resulting amines. For instance, up to 39% of the N,N-dimethylamine derivative shown in Figure 1 was obtained from 5b under these conditions.
-
-
-
-
40
-
-
0001551621
-
-
Chinchilla, R.; Falvello, L. R.; Nájera, C. J. Org. Chem. 1996, 61, 1, 7285.
-
(1996)
J. Org. Chem.
, vol.61
, Issue.1
, pp. 7285
-
-
Chinchilla, R.1
Falvello, L.R.2
Nájera, C.3
-
41
-
-
0004133516
-
-
Gaussian, Inc.: Pittsburgh, PA
-
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria G. E.; Robb M. A.; Cheeseman J. R.; Zakrzewski V. G.; Montgomery J. A.; Stratmann R. E.; Burant J. C.; Dapprich S.; Millam J. M.; Daniels A. D.; Kudin K. N.; Strain M. C.; Farkas O.; Tomasi J.; Barone V.; Cossi M.; Cammi R.; Mennucci B.; Pomelli C.; Adamo C.; Clifford S.; Ochterski J.; Petersson G. A.; Ayala P. Y.; Cui Q.; Morokuma K.; Malick D. K.; Rabuck A. D.; Raghavachari K.; Foresman J. B.; Cioslowski J.; Ortiz J. V.; Stefanov B. B.; Liu G.; Liashenko A.; Piskorz P.; Komaromi I.; Gomperta R.; Martin R. L.; Fox D. J.; Keith T.; Al-Laham M. A.; Peng C. Y.; Nanayakkara A.; Gonzalez C.; Challacombe M.; Gill P. M. W.; Johnson B. G.; Chen W.; Wong M. W.; Andres J. L.; Head-Gordon M.; Replogle E. S.; Pople J. A. Gaussian 98W (Revision A.3); Gaussian, Inc.: Pittsburgh, PA, 1998.
-
(1998)
Gaussian 98W (Revision A.3)
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery, J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperta, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkara, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.G.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Head-Gordon, M.55
Replogle, E.S.56
Pople, J.A.57
more..
-
42
-
-
0347170005
-
-
(a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
-
(1972)
J. Chem. Phys.
, vol.56
, pp. 2257
-
-
Hehre, W.J.1
Ditchfield, R.2
Pople, J.A.3
-
43
-
-
49649133169
-
-
(a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
-
(1972)
Chem. Phys. Lett.
, vol.66
, pp. 217
-
-
Hariharan, P.C.1
Pople, J.A.2
-
46
-
-
0345491105
-
-
(c) Lee, C.; Yang, W. Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
47
-
-
0345034039
-
-
Unpublished results
-
In full analogy with enamines, the nucleophilic character of the azomethine carbon of hydrazones demands an effective conjugation between the amino nitrogen and the CN double bond. Consequently, the electrophilic, imine-like reactivity of hydrazones requires the loss of conjugation and, hence, conformations clearly deviated from planarity. Pappalardo, R. R.; Muñoz, J. M.; Fernández, R.; Lassaletta, J. M., Unpublished results.
-
-
-
Pappalardo, R.R.1
Muñoz, J.M.2
Fernández, R.3
Lassaletta, J.M.4
|