-
4
-
-
3042663164
-
-
(a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837.
-
(2004)
Curr. Med. Chem
, vol.11
, pp. 1837
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
-
5
-
-
0032707721
-
-
(b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223.
-
(1999)
Eur. J. Org. Chem
, pp. 3223
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
-
6
-
-
33646544385
-
-
(c) Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 6060
-
-
Jiao, L.1
Liang, Y.2
Xu, J.3
-
7
-
-
0034674972
-
-
(a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III.; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 7831
-
-
Taggi, A.E.1
Hafez, A.M.2
Wack, H.3
Young, B.4
Drury III, W.J.5
Lectka, T.6
-
8
-
-
0037067063
-
-
(b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 6626
-
-
Taggi, A.E.1
Hafez, A.M.2
Wack, H.3
Young, B.4
Ferraris, D.5
Lectka, T.6
-
12
-
-
4143125756
-
-
(f) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
-
(2004)
Acc. Chem. Res
, vol.37
, pp. 592
-
-
France, S.1
Weatherwax, A.2
Taggi, A.E.3
Lectka, T.4
-
13
-
-
13644264785
-
-
(g) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 1206
-
-
France, S.1
Shah, M.H.2
Weatherwax, A.3
Wack, H.4
Roth, J.P.5
Lectka, T.6
-
14
-
-
24044436551
-
-
(h) Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11586.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 11586
-
-
Lee, E.C.1
Hodous, B.L.2
Bergin, E.3
Shih, C.4
Fu, G.C.5
-
15
-
-
38749111840
-
-
(i) Zhang, Y.-R.; He, L.; Wu, X.; Shao, P.-L.; Ye, S. Org. Lett. 2008, 10, 277.
-
(2008)
Org. Lett
, vol.10
, pp. 277
-
-
Zhang, Y.-R.1
He, L.2
Wu, X.3
Shao, P.-L.4
Ye, S.5
-
16
-
-
47949123042
-
-
(j) Duguet, N.; Campbell, C. D.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1108.
-
(2008)
Org. Biomol. Chem
, vol.6
, pp. 1108
-
-
Duguet, N.1
Campbell, C.D.2
Slawin, A.M.Z.3
Smith, A.D.4
-
17
-
-
0035215545
-
-
For leading references on the chemistry of β-lactams, see: a
-
For leading references on the chemistry of β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813.
-
(2001)
Synlett
, pp. 1813
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
-
18
-
-
3042619331
-
-
(b) Deshmukh, A. R. A. S.; Bhawal, B. M.; Krishnaswamy, D.; Govande, V. V.; Shinkre, B. A.; Jayanthi, A. Curr. Med. Chem. 2004, 11, 1889.
-
(2004)
Curr. Med. Chem
, vol.11
, pp. 1889
-
-
Deshmukh, A.R.A.S.1
Bhawal, B.M.2
Krishnaswamy, D.3
Govande, V.V.4
Shinkre, B.A.5
Jayanthi, A.6
-
21
-
-
0004030277
-
-
For leading references on the biological activity of β-lactams, see: a, Morin, R. B, Gorman, M, Eds, Academic Press: New York, Vols
-
For leading references on the biological activity of β-lactams, see: (a) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
-
(1982)
Chemistry and Biology of β-Lactam Antibiotics
, vol.1-3
-
-
-
25
-
-
0037176279
-
-
Recent uses of dichloroketene: (a) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313.
-
Recent uses of dichloroketene: (a) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313.
-
-
-
-
26
-
-
26844514473
-
-
(b) Roche, C.; Kadlecikova, K.; Veyron, A.; Delair, P.; Philouze, C.; Greene, A. E.; Flot, D.; Burghammer, M. J. Org. Chem. 2005, 70, 8352.
-
(2005)
J. Org. Chem
, vol.70
, pp. 8352
-
-
Roche, C.1
Kadlecikova, K.2
Veyron, A.3
Delair, P.4
Philouze, C.5
Greene, A.E.6
Flot, D.7
Burghammer, M.8
-
27
-
-
26844467151
-
-
(c) Padwa, A.; Nara, S.; Wang, Q. J. Org. Chem. 2005, 70, 8538.
-
(2005)
J. Org. Chem
, vol.70
, pp. 8538
-
-
Padwa, A.1
Nara, S.2
Wang, Q.3
-
28
-
-
15044354868
-
-
(d) Wang, Q.; Nara, S.; Padwa, A. Org. Lett. 2005, 7, 839.
-
(2005)
Org. Lett
, vol.7
, pp. 839
-
-
Wang, Q.1
Nara, S.2
Padwa, A.3
-
30
-
-
33750339111
-
-
(f) Ceccon, J.; Greene, A. E.; Poisson, J.-F. Org. Lett. 2006, 8, 4739.
-
(2006)
Org. Lett
, vol.8
, pp. 4739
-
-
Ceccon, J.1
Greene, A.E.2
Poisson, J.-F.3
-
31
-
-
33745055198
-
-
(g) Ussing, B. R.; Hang, C.; Singleton, D. A. J. Am. Chem. Soc. 2006, 128, 7594.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 7594
-
-
Ussing, B.R.1
Hang, C.2
Singleton, D.A.3
-
33
-
-
29244476042
-
-
(a) Van Brabant, W.; Dejaegher, Y.; De Kimpe, N. Pure Appl. Chem. 2005, 77, 2061.
-
(2005)
Pure Appl. Chem
, vol.77
, pp. 2061
-
-
Van Brabant, W.1
Dejaegher, Y.2
De Kimpe, N.3
-
34
-
-
0037023473
-
-
(b) Dejaegher, Y.; Mangelinckx, S.; De Kimpe, N. J. Org. Chem. 2002, 67, 2075.
-
(2002)
J. Org. Chem
, vol.67
, pp. 2075
-
-
Dejaegher, Y.1
Mangelinckx, S.2
De Kimpe, N.3
-
35
-
-
2542487726
-
-
Khajavi, M. S.; Sefidkon, F.; Hosseini, S. S. S. J. Chem. Res., Synop. 1998, 11, 724.
-
(1998)
J. Chem. Res., Synop
, vol.11
, pp. 724
-
-
Khajavi, M.S.1
Sefidkon, F.2
Hosseini, S.S.S.3
-
36
-
-
13844294095
-
-
Dejaegher, Y.; Denolf, B.; Stevens, C. V.; De Kimpe, N. Synthesis 2005, 193.
-
(2005)
Synthesis
, pp. 193
-
-
Dejaegher, Y.1
Denolf, B.2
Stevens, C.V.3
De Kimpe, N.4
-
38
-
-
0000448885
-
-
(a) Brady, W. T.; Liddell, H. G.; Vaughn, W. L. J. Org. Chem. 1966, 31, 626.
-
(1966)
J. Org. Chem
, vol.31
, pp. 626
-
-
Brady, W.T.1
Liddell, H.G.2
Vaughn, W.L.3
-
40
-
-
53049083800
-
-
The dehalogenation reaction of trichloroacetyl chloride in the presence of the Zn-Cu amalgam did not afford satisfactory results due to the decomposition of starting imines 1-3
-
The dehalogenation reaction of trichloroacetyl chloride in the presence of the Zn-Cu amalgam did not afford satisfactory results due to the decomposition of starting imines 1-3.
-
-
-
-
41
-
-
37349022185
-
-
N-Nosyl imines were also used in the Staudinger reaction with arylalkylketenes: Sereda, O.; Wilhelm, R. Synlett 2007, 19, 3032.
-
N-Nosyl imines were also used in the Staudinger reaction with arylalkylketenes: Sereda, O.; Wilhelm, R. Synlett 2007, 19, 3032.
-
-
-
-
42
-
-
53049087923
-
-
The best conditions were obtained using 2 equiv of base and slowly adding acetyl chloride (2 equiv) for 2 h, in order to avoid the decomposition and polymerization of dichloroketene
-
The best conditions were obtained using 2 equiv of base and slowly adding acetyl chloride (2 equiv) for 2 h, in order to avoid the decomposition and polymerization of dichloroketene.
-
-
-
-
43
-
-
0034624432
-
-
4Si at high temperature (73-89% yield): (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
-
4Si at high temperature (73-89% yield): (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
-
-
-
-
45
-
-
53049101090
-
-
The purification on both silica gel and aluminum oxide was not effective due to the decomposition of most products. Simple crystallization was more efficient
-
The purification on both silica gel and aluminum oxide was not effective due to the decomposition of most products. Simple crystallization was more efficient.
-
-
-
-
46
-
-
0034693178
-
-
This base should not attack the ketene because of its steric hindrance: Tennyson, R, Romo, D. J. Org. Chem. 2000, 65, 7248
-
This base should not attack the ketene because of its steric hindrance: Tennyson, R.; Romo, D. J. Org. Chem. 2000, 65, 7248.
-
-
-
-
47
-
-
53049101790
-
-
2-t-Bu), and catalysts (from 0.1 to 0.3 equiv) and addition modes of acyl chloride were tested. Nevertheless, no improvement in the enantiomeric excess was observed, leading to poorer results than the 20% ee achieved with TMS-quinidine. It is important to note that, in all assays, the reaction provided the β-lactam 4a in high conversion (>85%).
-
2-t-Bu), and catalysts (from 0.1 to 0.3 equiv) and addition modes of acyl chloride were tested. Nevertheless, no improvement in the enantiomeric excess was observed, leading to poorer results than the 20% ee achieved with TMS-quinidine. It is important to note that, in all assays, the reaction provided the β-lactam 4a in high conversion (>85%).
-
-
-
-
48
-
-
33744903961
-
-
(a) Van Driessche, B.; Van Brabandt, W.; D'hooghe, M.; Dejaegher, Y.; De Kimpe, N. Tetrahedron 2006, 62, 6882.
-
(2006)
Tetrahedron
, vol.62
, pp. 6882
-
-
Van Driessche, B.1
Van Brabandt, W.2
D'hooghe, M.3
Dejaegher, Y.4
De Kimpe, N.5
-
50
-
-
2442672853
-
-
Hu, W.-P.; Tsai, P.-C.; Hsu, M.-K.; Wang, J.-J. J. Org. Chem. 2004, 69, 3983.
-
(2004)
J. Org. Chem
, vol.69
, pp. 3983
-
-
Hu, W.-P.1
Tsai, P.-C.2
Hsu, M.-K.3
Wang, J.-J.4
-
52
-
-
0028230652
-
-
Pedregal, C.; Ezquerra, J.; Escribano, A.; Carreño, M. C.; Ruano, L. C. Tetrahedron Lett. 1994, 35, 2053.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 2053
-
-
Pedregal, C.1
Ezquerra, J.2
Escribano, A.3
Carreño, M.C.4
Ruano, L.C.5
-
54
-
-
85027424651
-
-
(b) Kurosawa, W.; Kan, T.; Fukuyama, T. Org. Synth. 2002, 79, 186.
-
(2002)
Org. Synth
, vol.79
, pp. 186
-
-
Kurosawa, W.1
Kan, T.2
Fukuyama, T.3
-
55
-
-
0029119899
-
-
(c) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetahedron Lett. 1995, 36, 6373.
-
(1995)
Tetahedron Lett
, vol.36
, pp. 6373
-
-
Fukuyama, T.1
Jow, C.-K.2
Cheung, M.3
-
56
-
-
53049096453
-
-
The deprotection of the N-nosyl group of 8 was never observed even when an excess of thiolate was used.
-
The deprotection of the N-nosyl group of 8 was never observed even when an excess of thiolate was used.
-
-
-
-
57
-
-
53049088780
-
-
2NEt, but no variation was observed after the addition of the bases in comparison with the starting imine.
-
2NEt, but no variation was observed after the addition of the bases in comparison with the starting imine.
-
-
-
-
58
-
-
53049089530
-
-
We were not able to detect any intermediate by in situ IR (see Supporting Information). On the other hand, a direct and fast transformation to β-lactam 4g was observed.
-
We were not able to detect any intermediate by in situ IR (see Supporting Information). On the other hand, a direct and fast transformation to β-lactam 4g was observed.
-
-
-
|