-
2
-
-
53549110712
-
-
Published online August 16, 2008
-
(b) Jones, G. O.; Li, X.; Hayden, A. D.; Houk, K. N.; Danishefsky, S. J. Org. Lett. Published online August 16, 2008, http://dx.doi.org/10.1021/ ol8016287.
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Org. Lett
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Jones, G.O.1
Li, X.2
Hayden, A.D.3
Houk, K.N.4
Danishefsky, S.J.5
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4
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0001521573
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-
(b) Ugi, I.; Meyr, R.; Fetzer, U.; Steinbrückner, C. Angew. Chem. 1959, 71, 386.
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(1959)
Angew. Chem
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Ugi, I.1
Meyr, R.2
Fetzer, U.3
Steinbrückner, C.4
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5
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26844537872
-
-
For reviews, see: c
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For reviews, see: (c) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
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(2005)
Org. React
, vol.65
, pp. 1
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Banfi, L.1
Riva, R.2
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6
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0001134412
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(d) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
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(2000)
Angew. Chem., Int. Ed
, vol.39
, pp. 3168
-
-
Dömling, A.1
Ugi, I.2
-
8
-
-
0041417143
-
-
The reaction described here is a special instance of a Mumm rearrangement which involves a 1,3-O→N acyl transfer not in the formimidate series. However, the formimidate context reported here renders this reaction unique. For literature access to the Mumm reaction, see: (a) Mumm, O.; Hesse, H.; Volquartz, H. Ber. 1915, 48, 379.
-
The reaction described here is a special instance of a Mumm rearrangement which involves a 1,3-O→N acyl transfer not in the formimidate series. However, the formimidate context reported here renders this reaction unique. For literature access to the Mumm reaction, see: (a) Mumm, O.; Hesse, H.; Volquartz, H. Ber. 1915, 48, 379.
-
-
-
-
12
-
-
0034712246
-
-
(e) Darbeau, R. W.; White, E. H.; Nunez, N.; Coit, B.; Daigle, M. J. Org. Chem. 2000, 65, 1115.
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(2000)
J. Org. Chem
, vol.65
, pp. 1115
-
-
Darbeau, R.W.1
White, E.H.2
Nunez, N.3
Coit, B.4
Daigle, M.5
-
13
-
-
53549135148
-
-
In our first paper in this series ref 1, we described a direct pathway to 4, via a formal cycloaddition pathway, which does not pass through 3. In this paper, we focus on the presumed pathway from 3 to 4. However, involvement of the direct cycloaddition pathway to reach 4 is not ruled out
-
In our first paper in this series (ref 1), we described a direct pathway to 4, via a formal cycloaddition pathway, which does not pass through 3. In this paper, we focus on the presumed pathway from 3 to 4. However, involvement of the direct cycloaddition pathway to reach 4 is not ruled out.
-
-
-
-
14
-
-
34547492323
-
-
(a) Shaabani, A.; Soleimani, E.; Rezayan, A. H. Tetrahedron Lett. 2007, 48, 6137.
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 6137
-
-
Shaabani, A.1
Soleimani, E.2
Rezayan, A.H.3
-
17
-
-
0003581236
-
-
(d) Shono, T.; Kimura, M.; Ito, Y.; Nishida, K.; Oda, R. Bull. Chem. Soc. Jpn. 1964, 37, 635.
-
(1964)
Bull. Chem. Soc. Jpn
, vol.37
, pp. 635
-
-
Shono, T.1
Kimura, M.2
Ito, Y.3
Nishida, K.4
Oda, R.5
-
18
-
-
34249088907
-
-
The structure was presumed on the basis of its infrared spectrum, (e) Isaka, M.; Boonkhao, B.; Rachtawee, P.; Auncharoen, P. J. Nat. Prod. 2007, 70,
-
The structure was presumed on the basis of its infrared spectrum, (e) Isaka, M.; Boonkhao, B.; Rachtawee, P.; Auncharoen, P. J. Nat. Prod. 2007, 70,
-
-
-
-
19
-
-
84971086544
-
-
For cyclic structures of formimidate-carboxylate mixed anhydride, see: f
-
For cyclic structures of formimidate-carboxylate mixed anhydride, see: (f) Black, D. S. C.; Boscacci, A. B. Aus. J. Chem. 1977, 30, 1109.
-
(1977)
Aus. J. Chem
, vol.30
, pp. 1109
-
-
Black, D.S.C.1
Boscacci, A.B.2
-
20
-
-
53549115001
-
-
(g) Kobayashi, S.; Tsukamoto, Y.; Saegusa, T. Macromolecules 1990, 23, 2608.
-
(1990)
Macromolecules
, vol.23
, pp. 2608
-
-
Kobayashi, S.1
Tsukamoto, Y.2
Saegusa, T.3
-
22
-
-
0001441712
-
-
(i) Gomory, A.; Somogyi, A.; Tamas, J.; Stajer, G.; Bernath, G.; Komaromi, I. Int. J. Mass Spec. Ion Proc. 1991, 107, 225.
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(1991)
Int. J. Mass Spec. Ion Proc
, vol.107
, pp. 225
-
-
Gomory, A.1
Somogyi, A.2
Tamas, J.3
Stajer, G.4
Bernath, G.5
Komaromi, I.6
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23
-
-
45749083425
-
-
In some instances, spectroscopic suggestion of such an intermediate has been described, for example: (a) Hou, J-L.; Ajami, D.; Rebek, J., Jr J. Am. Chem. Soc. 2008, 130, 7810.
-
In some instances, spectroscopic suggestion of such an intermediate has been described, for example: (a) Hou, J-L.; Ajami, D.; Rebek, J., Jr J. Am. Chem. Soc. 2008, 130, 7810.
-
-
-
-
25
-
-
84978981855
-
-
Greater progress in characterization has been achieved with related mixed anhydrides which are not in the formimidate series, cf. inter alia: (a) Kawasaki, K, Tsumura, S, Katsuki, T. Synlett. 1995, 12, 1245
-
Greater progress in characterization has been achieved with related mixed anhydrides which are not in the formimidate series, cf. inter alia: (a) Kawasaki, K.; Tsumura, S.; Katsuki, T. Synlett. 1995, 12, 1245.
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-
-
-
27
-
-
37049138028
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-
(c) Cambie, R. C.; Hayward, R. C.; Roberts, J. L.; Rutledge, P. S. J. Chem. Soc., Perkin Transe. 1 1974, 15, 1858.
-
(1974)
J. Chem. Soc., Perkin Transe. 1
, vol.15
, pp. 1858
-
-
Cambie, R.C.1
Hayward, R.C.2
Roberts, J.L.3
Rutledge, P.S.4
-
28
-
-
53549129149
-
-
-1 for the alleged mixed anhydride 7.
-
-1 for the alleged mixed anhydride 7.
-
-
-
-
29
-
-
53549111268
-
-
Typical IR absorptions reported for a nonformimidate mixed anhydride of the type 7 are ca. 1710-1660 cm-1; see ref 7
-
-1; see ref 7.
-
-
-
-
30
-
-
0000443935
-
-
The NMR spectrum of the diffraction worthy crystal is the same as that of the bulk material. For a crystal structure based on a hydrogen-bonded complex between two small molecules, see
-
The NMR spectrum of the diffraction worthy crystal is the same as that of the bulk material. For a crystal structure based on a hydrogen-bonded complex between two "small molecules", see: Leiserowitz, L.; Nader, F. Acta Crystallogr. 1977, B33, 2719.
-
(1977)
Acta Crystallogr
, vol.B33
, pp. 2719
-
-
Leiserowitz, L.1
Nader, F.2
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32
-
-
0010479339
-
-
(b) Cooley, J. H.; Stone, D. M.; Oguri, H. J. Org. Chem. 1977, 42, 3096.
-
(1977)
J. Org. Chem
, vol.42
, pp. 3096
-
-
Cooley, J.H.1
Stone, D.M.2
Oguri, H.3
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35
-
-
84981807517
-
-
(e) Fernholz, H.; Schmidt, H. J. Angew. Chem., Int. Ed. 1969, 8, 521.
-
(1969)
Angew. Chem., Int. Ed
, vol.8
, pp. 521
-
-
Fernholz, H.1
Schmidt, H.J.2
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36
-
-
33750457003
-
-
(f) Callens, E.; Burton, A. J.; Barrett, A. G. M. Tetrahedron Lett. 2006, 47, 8699.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 8699
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-
Callens, E.1
Burton, A.J.2
Barrett, A.G.M.3
-
37
-
-
0034549338
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-
(g) Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
-
(2000)
J. Org. Chem
, vol.65
, pp. 8210
-
-
Katritzky, A.R.1
He, H.-Y.2
Suzuki, K.3
-
43
-
-
0035806182
-
-
(d) Kotha, S.; Screenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg. Med. Chem. Lett. 2001, 11, 1421.
-
(2001)
Bioorg. Med. Chem. Lett
, vol.11
, pp. 1421
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-
Kotha, S.1
Screenivasachary, N.2
Mohanraja, K.3
Durani, S.4
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44
-
-
53549135687
-
-
Microwave heating of Gloede's product (purported 15) in chloroform again failed to produce the desired N-formylamide.
-
Microwave heating of Gloede's product (purported 15) in chloroform again failed to produce the desired N-formylamide.
-
-
-
-
45
-
-
53549103793
-
-
It should be noted that the elemental analysis, N, 10.45, ref 3b of Gloede's product 15 (calcd, N, 10.14) fits better for compound 17 (calcd, N, 10.33) than that concluded by Gloede. As reported by the authors, the claimed 15 does not react with methanol under reflux conditions
-
It should be noted that the elemental analysis, "%N = 10.45," (ref 3b) of Gloede's product 15 (calcd % N = 10.14) fits better for compound 17 (calcd. %N = 10.33) than that concluded by Gloede. As reported by the authors, the claimed 15 does not react with methanol under reflux conditions.
-
-
-
-
46
-
-
0010519267
-
-
Authentic 1,3-dicyclohexylamidine (18) was prepared according to a known procedure: Taylor, E. C.; Ehrhart, W. A. J. Org. Chem. 1963, 28, 1108.
-
Authentic 1,3-dicyclohexylamidine (18) was prepared according to a known procedure: Taylor, E. C.; Ehrhart, W. A. J. Org. Chem. 1963, 28, 1108.
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-
-
-
49
-
-
13844284344
-
-
(b) Olguín, L. F.; Jiménez-Estrada, M.; Bárzana, E.; Navarro-Ocaña, A. Synlett 2005, 2, 340.
-
(2005)
Synlett
, vol.2
, pp. 340
-
-
Olguín, L.F.1
Jiménez-Estrada, M.2
Bárzana, E.3
Navarro-Ocaña, A.4
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50
-
-
46549104725
-
-
This concept was suggested to account for the small amount of amide formation at room temperature; see ref 1. For cyclization examples that do not follow Baldwin's rule, see: Astudillo, M. E. A, Chokotho, N. C. J, Jarvis, T. C, Johnson, C. D, Lewis, C. C, McDonnel, P. D. Tetrahedron 1985, 41, 5919
-
This concept was suggested to account for the small amount of amide formation at room temperature; see ref 1. For cyclization examples that do not follow Baldwin's rule, see: Astudillo, M. E. A.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnel, P. D. Tetrahedron 1985, 41, 5919.
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-
-
-
51
-
-
53549105749
-
-
Both isonitriles 25 and 27 were prepared in racemic form.
-
Both isonitriles 25 and 27 were prepared in racemic form.
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-
-
-
52
-
-
49149087660
-
-
Okamoto, R.; Kajihara, Y. Angew. Chem., Int. Ed. 2008, 47, 5402.
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(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 5402
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Okamoto, R.1
Kajihara, Y.2
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