-
3
-
-
0026000562
-
-
Whitten, J. P.; Muench, D.; Cube, R. V.; Nyce, P. L.; Baron, B. M.; McDonald, I. A. Bioorg. Med. Chem. Lett. 1991, 1, 441
-
(1991)
Bioorg. Med. Chem. Lett.
, vol.1
, pp. 441
-
-
Whitten, J.P.1
Muench, D.2
Cube, R.V.3
Nyce, P.L.4
Baron, B.M.5
McDonald, I.A.6
-
6
-
-
0037473504
-
-
Amos, D. T.; Renslo, A. R.; Danheiser, R. L. J. Am. Chem. Soc. 2003, 125, 4970
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 4970
-
-
Amos, D.T.1
Renslo, A.R.2
Danheiser, R.L.3
-
7
-
-
75749146979
-
-
Airiau, E.; Spangenberg, T.; Girard, N.; Breit, B.; Mann, A. Org. Lett. 2010, 12, 528
-
(2010)
Org. Lett.
, vol.12
, pp. 528
-
-
Airiau, E.1
Spangenberg, T.2
Girard, N.3
Breit, B.4
Mann, A.5
-
11
-
-
33847005954
-
-
Zou, W.; Sandbhor, M.; Bhasin, M. J. Org. Chem. 2007, 72, 1226
-
(2007)
J. Org. Chem.
, vol.72
, pp. 1226
-
-
Zou, W.1
Sandbhor, M.2
Bhasin, M.3
-
12
-
-
4644299866
-
-
Ma, S.; Ni, B.; Liang, Z. J. Org. Chem. 2004, 69, 6305
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6305
-
-
Ma, S.1
Ni, B.2
Liang, Z.3
-
13
-
-
57149125464
-
-
Auruaym, E.; Spangenberg, T.; Girard, N.; Schoenfelder, A.; Salvadori, J.; Taddei, M.; Mann, A. Chem.-Eur. J. 2008, 14, 10938
-
(2008)
Chem.-Eur. J.
, vol.14
, pp. 10938
-
-
Auruaym, E.1
Spangenberg, T.2
Girard, N.3
Schoenfelder, A.4
Salvadori, J.5
Taddei, M.6
Mann, A.7
-
15
-
-
62049085800
-
-
Amorde, S. M.; Jewett, I.; Martin, S. F. Tetrahedron 2009, 65, 3222
-
(2009)
Tetrahedron
, vol.65
, pp. 3222
-
-
Amorde, S.M.1
Jewett, I.2
Martin, S.F.3
-
16
-
-
78650370488
-
-
Fang, H.; Wu, X.; Nie, L.; Dai, X.; Chen, J.; Cao, W.; Zhao, G. Org. Lett. 2010, 12, 5366
-
(2010)
Org. Lett.
, vol.12
, pp. 5366
-
-
Fang, H.1
Wu, X.2
Nie, L.3
Dai, X.4
Chen, J.5
Cao, W.6
Zhao, G.7
-
17
-
-
33748994796
-
-
Bélanger, G.; Doré, M.; Ménard, F.; Darsigny, V. J. Org. Chem. 2006, 71, 7481
-
(2006)
J. Org. Chem.
, vol.71
, pp. 7481
-
-
Bélanger, G.1
Doré, M.2
Ménard, F.3
Darsigny, V.4
-
18
-
-
26444461419
-
-
Bélanger, G.; Larouche-Gauthier, R.; Ménard, F.; Nantel, M.; Barabé, F. Org. Lett. 2005, 7, 4431
-
(2005)
Org. Lett.
, vol.7
, pp. 4431
-
-
Bélanger, G.1
Larouche-Gauthier, R.2
Ménard, F.3
Nantel, M.4
Barabé, F.5
-
19
-
-
30744440409
-
-
Bélanger, G.; Larouche-Gauthier, R.; Ménard, F.; Nantel, M.; Barabé, F. J. Org. Chem. 2006, 71, 704
-
(2006)
J. Org. Chem.
, vol.71
, pp. 704
-
-
Bélanger, G.1
Larouche-Gauthier, R.2
Ménard, F.3
Nantel, M.4
Barabé, F.5
-
21
-
-
33846312573
-
-
The first example of double intramolecular nucleophilic trapping of activated amides was reported by our group (ref 11). The single closest related example is the activation of a carbamate and subsequent nucleophilic trapping. See
-
The first example of double intramolecular nucleophilic trapping of activated amides was reported by our group (ref 11). The single closest related example is the activation of a carbamate and subsequent nucleophilic trapping. See: Magnus, P.; Gazzard, L.; Hobson, L.; Payne, A. H.; Rainey, T. J.; Westlund, N.; Lynch, V. Tetrahedron 2002, 58, 3423
-
(2002)
Tetrahedron
, vol.58
, pp. 3423
-
-
Magnus, P.1
Gazzard, L.2
Hobson, L.3
Payne, A.H.4
Rainey, T.J.5
Westlund, N.6
Lynch, V.7
-
22
-
-
0038292651
-
-
When the nucleophile is an indole or an aryle, the reaction is rather called a Bischler-Napieralski cyclization
-
When the nucleophile is an indole or an aryle, the reaction is rather called a Bischler-Napieralski cyclization: Bischler, A.; Napieralski, B. Chem. Ber. 1893, 26, 903
-
(1893)
Chem. Ber.
, vol.26
, pp. 903
-
-
Bischler, A.1
Napieralski, B.2
-
23
-
-
29144475769
-
-
Since thorough degassing of the reaction mixture to remove oxygen prior to addition of triflic anhydride did not prevent the formation of pyridinium 13 the oxidation is believed to occur via deprotonation of eniminium 12 and oxidation of the resulting 1,2-dihydropyridine by hydride transfer to reduce iminium species in solution and to generate pyridinium 13. For an example of oxidation of 1,2-dihydropyridine to pyridinium ion via hydride transfer, see
-
Since thorough degassing of the reaction mixture to remove oxygen prior to addition of triflic anhydride did not prevent the formation of pyridinium 13 the oxidation is believed to occur via deprotonation of eniminium 12 and oxidation of the resulting 1,2-dihydropyridine by hydride transfer to reduce iminium species in solution and to generate pyridinium 13. For an example of oxidation of 1,2-dihydropyridine to pyridinium ion via hydride transfer, see: Cattoe, X.; Bourissoua, D.; Bertrand, G. Tetrahedron 2006, 47, 531
-
(2006)
Tetrahedron
, vol.47
, pp. 531
-
-
Cattoe, X.1
Bourissoua, D.2
Bertrand, G.3
-
24
-
-
0037241494
-
-
We observed the following decreasing order of nucleophilicity: allylstannane > allylsilane with non-substituted nucleophilic carbon (cf. 1a) > allylsilane with substituted nucleophilic carbon (cf. 9) > vinylsilane. This order is in accord with Mayr's calculated nucleophilicity of carbon nucleophiles. See
-
We observed the following decreasing order of nucleophilicity: allylstannane > allylsilane with non-substituted nucleophilic carbon (cf. 1a) > allylsilane with substituted nucleophilic carbon (cf. 9) > vinylsilane. This order is in accord with Mayr's calculated nucleophilicity of carbon nucleophiles. See: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66
-
(2003)
Acc. Chem. Res.
, vol.36
, pp. 66
-
-
Mayr, H.1
Kempf, B.2
Ofial, A.R.3
-
25
-
-
58049202981
-
-
We do not have a clear explanation to why, in this case, we observed a competitive deprotonation to 16. We could presume that the vinyl group induces a conformation in which the indicated proton in 26 (Scheme 3) is acidified due to a better alignment with the p orbital of the carbocation. For another recent example of competition between desilylation and deprotonation, see
-
We do not have a clear explanation to why, in this case, we observed a competitive deprotonation to 16. We could presume that the vinyl group induces a conformation in which the indicated proton in 26 (Scheme 3) is acidified due to a better alignment with the p orbital of the carbocation. For another recent example of competition between desilylation and deprotonation, see: Lee, M. H.; Nieto-Oberhuber, C.; Shair, D. M. J. Am. Chem. Soc. 2008, 130, 16864
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 16864
-
-
Lee, M.H.1
Nieto-Oberhuber, C.2
Shair, D.M.3
|