-
1
-
-
34250653953
-
-
For recent reviews on [2+2+2] cycloaddition, see: a B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085;
-
For recent reviews on [2+2+2] cycloaddition, see: a) B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085;
-
-
-
-
7
-
-
49749094562
-
-
Ed, L. E. Overman, Wiley, Hoboken
-
g) N. Agenet, O. Buisine, F. Slowinski, V. Gondon, C. Aubert, M. Malacria, Organic Reactions, Vol. 68 (Ed.: L. E. Overman), Wiley, Hoboken, 2007, p. 1.
-
(2007)
Organic Reactions
, vol.68
, pp. 1
-
-
Agenet, N.1
Buisine, O.2
Slowinski, F.3
Gondon, V.4
Aubert, C.5
Malacria, M.6
-
8
-
-
85023357778
-
-
For the use of stoichiometric Co reagents, see: a
-
For the use of stoichiometric Co reagents, see: a) D. F. Harvey, B. M. Johnson, C. S. Ung, K. P. C. Vollhardt, Synlett 1989, 15;
-
(1989)
Synlett
, pp. 15
-
-
Harvey, D.F.1
Johnson, B.M.2
Ung, C.S.3
Vollhardt, K.P.C.4
-
10
-
-
0037138686
-
-
for the use of stoichiometric zirconacyclopentadienes, see: c
-
for the use of stoichiometric zirconacyclopentadienes, see: c) T. Takahashi, Y. Li, T. Ito, F. Xu, K. Nakajima, Y. Liu, J. Am. Chem. Soc. 2002, 124, 1144.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 1144
-
-
Takahashi, T.1
Li, Y.2
Ito, T.3
Xu, F.4
Nakajima, K.5
Liu, Y.6
-
11
-
-
33845278591
-
-
For pioneering work on Ni catalysis, see: a
-
For pioneering work on Ni catalysis, see: a) T. Tsuda, T. Kiyoi, T. Miyane, T. Saegusa, J. Am. Chem. Soc. 1988, 110, 8570;
-
(1988)
J. Am. Chem. Soc
, vol.110
, pp. 8570
-
-
Tsuda, T.1
Kiyoi, T.2
Miyane, T.3
Saegusa, T.4
-
12
-
-
24944526271
-
-
0/imidazolylidene complexes, see: b T. N. Tekevac, J. Louie, Org. Lett. 2005, 7, 4037;
-
0/imidazolylidene complexes, see: b) T. N. Tekevac, J. Louie, Org. Lett. 2005, 7, 4037;
-
-
-
-
13
-
-
33644559029
-
-
for the Ni-catalyzed [4+2+2] cycloaddition of 1,6-diynes with cyclobutanones, see: c M. Murakami, S. Ashida, T. Matsuda, J. Am. Chem. Soc. 2006, 128, 2166.
-
for the Ni-catalyzed [4+2+2] cycloaddition of 1,6-diynes with cyclobutanones, see: c) M. Murakami, S. Ashida, T. Matsuda, J. Am. Chem. Soc. 2006, 128, 2166.
-
-
-
-
14
-
-
0037134815
-
-
For pioneering work on Ru catalysis, see: a
-
For pioneering work on Ru catalysis, see: a) Y. Yamamoto, H. Takagishi, K. Itoh, J. Am. Chem. Soc. 2002, 124, 6844;
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 6844
-
-
Yamamoto, Y.1
Takagishi, H.2
Itoh, K.3
-
15
-
-
0034697670
-
-
II-catalyzed hydrative cyclization and [4+2] cycloaddition of yne-enones, see: b B. M. Trost, R. E. Brown, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 5877.
-
II-catalyzed hydrative cyclization and [4+2] cycloaddition of yne-enones, see: b) B. M. Trost, R. E. Brown, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 5877.
-
-
-
-
16
-
-
29444459761
-
-
2]-catalyzed intramolecular [2+2+2] cycloaddition of diynals (cod=1,5-cyclooctadiene), see: a) B. Bennacer, M. Fujiwara, S.-Y. Lee, I. Ojima, J. Am. Chem. Soc. 2005, 127, 17756;
-
2]-catalyzed intramolecular [2+2+2] cycloaddition of diynals (cod=1,5-cyclooctadiene), see: a) B. Bennacer, M. Fujiwara, S.-Y. Lee, I. Ojima, J. Am. Chem. Soc. 2005, 127, 17756;
-
-
-
-
17
-
-
33845585619
-
-
I+/biphep-catalyzed carbonyl Z dienylation involving carbonyl insertion into cationic rhodacyclopentadienes (biphep=2,2′-bis(diphenylphosphanyl)-1,1′-biphenyl), see: b) J. R. Kong, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16040.
-
I+/biphep-catalyzed carbonyl Z dienylation involving carbonyl insertion into cationic rhodacyclopentadienes (biphep=2,2′-bis(diphenylphosphanyl)-1,1′-biphenyl), see: b) J. R. Kong, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16040.
-
-
-
-
18
-
-
32644439884
-
-
For recent reviews of catalytic asymmetric methods for the generation of quaternary carbon centers, see: a
-
For recent reviews of catalytic asymmetric methods for the generation of quaternary carbon centers, see: a) B. M. Trost, C. Jiang, Synthesis 2006, 369;
-
(2006)
Synthesis
, pp. 369
-
-
Trost, B.M.1
Jiang, C.2
-
21
-
-
53549135690
-
-
For the Au-catalyzed diastereoselective intermolecular addition of carbonyl compounds to 1,6-enynes to give fused [5,5] ring systems, see: M. Schelwies, A. L. Dempwolff, F. Rominger, G. Helmchen, Angew. Chem. 2007, 119, 5694;
-
For the Au-catalyzed diastereoselective intermolecular addition of carbonyl compounds to 1,6-enynes to give fused [5,5] ring systems, see: M. Schelwies, A. L. Dempwolff, F. Rominger, G. Helmchen, Angew. Chem. 2007, 119, 5694;
-
-
-
-
23
-
-
34250645784
-
-
a) K. Tanaka, Y. Otake, A. Wada, K. Noguchi, M. Hirano, Org. Lett. 2007, 9, 2203;
-
(2007)
Org. Lett
, vol.9
, pp. 2203
-
-
Tanaka, K.1
Otake, Y.2
Wada, A.3
Noguchi, K.4
Hirano, M.5
-
24
-
-
34250783250
-
-
a similar publication appeared soon afterwards: b K. Tsuchikama, Y. Yoshinami, T. Shibata, Synlett 2007, 1395.
-
a similar publication appeared soon afterwards: b) K. Tsuchikama, Y. Yoshinami, T. Shibata, Synlett 2007, 1395.
-
-
-
-
25
-
-
0346780615
-
-
I/modified- binap complexes, see: a K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697;
-
I/modified- binap complexes, see: a) K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697;
-
-
-
-
26
-
-
20744434691
-
-
b) K. Tanaka, G. Nishida, A. Wada, K. Noguchi, Angew. Chem. 2004, 116, 6672;
-
(2004)
Angew. Chem
, vol.116
, pp. 6672
-
-
Tanaka, K.1
Nishida, G.2
Wada, A.3
Noguchi, K.4
-
28
-
-
14544299221
-
-
c) K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J. 2005, 11, 1145;
-
(2005)
Chem. Eur. J
, vol.11
, pp. 1145
-
-
Tanaka, K.1
Toyoda, K.2
Wada, A.3
Shirasaka, K.4
Hirano, M.5
-
29
-
-
33646053203
-
-
d) K. Tanaka, K. Takeishi, K. Noguchi, J. Am. Chem. Soc. 2006, 128, 4586;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 4586
-
-
Tanaka, K.1
Takeishi, K.2
Noguchi, K.3
-
30
-
-
33846953245
-
-
e) K. Tanaka, H. Sagae, K. Toyoda, K. Noguchi, M. Hirano, J. Am. Chem. Soc. 2007, 129, 1522;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 1522
-
-
Tanaka, K.1
Sagae, H.2
Toyoda, K.3
Noguchi, K.4
Hirano, M.5
-
31
-
-
53349134274
-
-
f) G. Nishida, K. Noguchi, M. Hirano, K. Tanaka, Angew. Chem. 2007, 119, 4025;
-
(2007)
Angew. Chem
, vol.119
, pp. 4025
-
-
Nishida, G.1
Noguchi, K.2
Hirano, M.3
Tanaka, K.4
-
32
-
-
34250771917
-
-
and references therein;
-
Angew. Chem. Int. Ed. 2007, 46, 3951, and references therein;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 3951
-
-
-
33
-
-
33748550638
-
-
for similar reactions of nitriles, see: g
-
for similar reactions of nitriles, see: g) K. Tanaka, N. Suzuki, G. Nishida, Eur. J. Org. Chem. 2006, 3917;
-
(2006)
Eur. J. Org. Chem
, pp. 3917
-
-
Tanaka, K.1
Suzuki, N.2
Nishida, G.3
-
34
-
-
34147113797
-
-
h) A. Wada, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett. 2007, 9, 1295;
-
(2007)
Org. Lett
, vol.9
, pp. 1295
-
-
Wada, A.1
Noguchi, K.2
Hirano, M.3
Tanaka, K.4
-
35
-
-
27144521700
-
-
for similar reactions of isocyanates and isothiocyanates, see: i
-
for similar reactions of isocyanates and isothiocyanates, see: i) K. Tanaka, A. Wada, K. Noguchi, Org. Lett. 2005, 7, 4737;
-
(2005)
Org. Lett
, vol.7
, pp. 4737
-
-
Tanaka, K.1
Wada, A.2
Noguchi, K.3
-
36
-
-
33644961738
-
-
j) K. Tanaka, A. Wada, K. Noguchi, Org. Lett. 2006, 8, 907;
-
(2006)
Org. Lett
, vol.8
, pp. 907
-
-
Tanaka, K.1
Wada, A.2
Noguchi, K.3
-
37
-
-
34250727598
-
-
for similar reactions of alkenes, see: k
-
for similar reactions of alkenes, see: k) K. Tanaka, G. Nishida, H. Sagae, M. Hirano, Synlett 2007, 1426.
-
(2007)
Synlett
, pp. 1426
-
-
Tanaka, K.1
Nishida, G.2
Sagae, H.3
Hirano, M.4
-
38
-
-
24744435554
-
-
We investigated the chemoselectivity of the present cycloaddition with respect to the reactivity of a carbonyl group in the presence of an alkyne moiety and found that the carbonyl group of an alkynyl ketoester reacted with a 1,6-enyne, although the cycloadduct could not be isolated in pure form. For the [2+2+2] cycloaddition of 1,6-enynes with monoalkynes under the catalysis of cationic complexes of RhI with modified binap ligands, see: a P. A. Evans, K. W. Lai, J. R. Sawyer, J. Am. Chem. Soc. 2005, 127, 12466;
-
I with modified binap ligands, see: a) P. A. Evans, K. W. Lai, J. R. Sawyer, J. Am. Chem. Soc. 2005, 127, 12466;
-
-
-
-
39
-
-
27644587938
-
-
Chemical Presented
-
b) T. Shibata, Y. Arai, Y. Tahara, Org. Lett. 2005, 7, 4955. (Chemical Presented)
-
(2005)
Org. Lett
, vol.7
, pp. 4955
-
-
Shibata, T.1
Arai, Y.2
Tahara, Y.3
-
40
-
-
53549134191
-
-
When the ligand (R)-binap was used, the cycloaddition products were obtained in higher yields than with (R)-H8-binap.
-
When the ligand (R)-binap was used, the cycloaddition products were obtained in higher yields than with (R)-H8-binap.
-
-
-
-
41
-
-
0034609662
-
-
Similar heterocycle formation during the transition-metal-catalyzed cycloisomerization of enynes was reported; for Ru, see: a M. Mori, Y. Kozawa, M. Ishida, M. Kanamaru, K. Onozuka, M. Takimoto, Org. Lett. 2000, 2, 3245;
-
Similar heterocycle formation during the transition-metal-catalyzed cycloisomerization of enynes was reported; for Ru, see: a) M. Mori, Y. Kozawa, M. Ishida, M. Kanamaru, K. Onozuka, M. Takimoto, Org. Lett. 2000, 2, 3245;
-
-
-
-
42
-
-
0035902860
-
-
for Co, see: b O. Buisine, C. Aubert, M. Malacria, Chem. Eur. J. 2001, 7, 3517;
-
for Co, see: b) O. Buisine, C. Aubert, M. Malacria, Chem. Eur. J. 2001, 7, 3517;
-
-
-
-
43
-
-
33646895444
-
-
for Rh, see: c H. Kawai, S. Oi, Y. Inoue, Heterocycles 2006, 67, 101;
-
for Rh, see: c) H. Kawai, S. Oi, Y. Inoue, Heterocycles 2006, 67, 101;
-
-
-
-
44
-
-
35048824311
-
-
d) K. Tanaka, Y. Otake, M. Hirano, Org. Lett. 2007, 9, 3953.
-
(2007)
Org. Lett
, vol.9
, pp. 3953
-
-
Tanaka, K.1
Otake, Y.2
Hirano, M.3
-
45
-
-
33750357709
-
-
I/modified-binap complex, see: K. Tsuchikama, Y. Kuwata, T. Shibata, J. Am. Chem. Soc. 2006, 128, 13686.
-
I/modified-binap complex, see: K. Tsuchikama, Y. Kuwata, T. Shibata, J. Am. Chem. Soc. 2006, 128, 13686.
-
-
-
-
46
-
-
53549108251
-
-
CCDC-662606 (3ab) and CCDC-662607 (6eh) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
CCDC-662606 (3ab) and CCDC-662607 (6eh) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
-
-
-
47
-
-
0001290656
-
-
For the Rh- or Ir-catalyzed dienylation of aromatic C-H bonds with alkynes, see: a
-
For the Rh- or Ir-catalyzed dienylation of aromatic C-H bonds with alkynes, see: a) M. C. Comstock, J. R. Shapley, Organometallics 1997, 16, 4816;
-
(1997)
Organometallics
, vol.16
, pp. 4816
-
-
Comstock, M.C.1
Shapley, J.R.2
-
48
-
-
0031571499
-
-
b) J. Müller, T. Akhnoukh, P. Escarpa Gaede, A. Guo, P. Moran, K. Qiao, J. Organomet. Chem. 1997, 541, 207;
-
(1997)
J. Organomet. Chem
, vol.541
, pp. 207
-
-
Müller, J.1
Akhnoukh, T.2
Escarpa Gaede, P.3
Guo, A.4
Moran, P.5
Qiao, K.6
-
49
-
-
33947085355
-
-
c) S. A. Gardner, P. S. Andrews, M. D. Rausch, Inorg. Chem. 1973, 12, 2396.
-
(1973)
Inorg. Chem
, vol.12
, pp. 2396
-
-
Gardner, S.A.1
Andrews, P.S.2
Rausch, M.D.3
-
50
-
-
34548763089
-
-
For the Co-mediated dienylation of aromatic C-H bonds with alkynes, see: a
-
For the Co-mediated dienylation of aromatic C-H bonds with alkynes, see: a) C. Aubert, P. Betschmann, M. J. Eichberg, V. Gandon, T. J. Heckrodt, J. Lehmann, M. Malacria, B. Masjost, E. Paredes, K. P. C. Vollhardt, G. D. Whitener, Chem. Eur. J. 2007, 13, 7443;
-
(2007)
Chem. Eur. J
, vol.13
, pp. 7443
-
-
Aubert, C.1
Betschmann, P.2
Eichberg, M.J.3
Gandon, V.4
Heckrodt, T.J.5
Lehmann, J.6
Malacria, M.7
Masjost, B.8
Paredes, E.9
Vollhardt, K.P.C.10
Whitener, G.D.11
-
51
-
-
0032784747
-
-
b) H. Pelissier, J. Rodriguez, K. P. C. Vollhardt, Chem. Eur. J. 1999, 5, 3549;
-
(1999)
Chem. Eur. J
, vol.5
, pp. 3549
-
-
Pelissier, H.1
Rodriguez, J.2
Vollhardt, K.P.C.3
-
52
-
-
0000420509
-
-
c) R. Boese, D. F. Harvey, M. J. Malaska, K. P. C. Vollhardt, J. Am. Chem. Soc. 1994, 116, 11153;
-
(1994)
J. Am. Chem. Soc
, vol.116
, pp. 11153
-
-
Boese, R.1
Harvey, D.F.2
Malaska, M.J.3
Vollhardt, K.P.C.4
-
56
-
-
34548709116
-
-
for theoretical studies, see: g
-
for theoretical studies, see: g) C. Aubert, V. Gandon, A. Geny, T. J. Heckrodt, M. Malacria, E. Paredes, K. P. C. Vollhardt, Chem. Eur. J. 2007, 13, 7466;
-
(2007)
Chem. Eur. J
, vol.13
, pp. 7466
-
-
Aubert, C.1
Gandon, V.2
Geny, A.3
Heckrodt, T.J.4
Malacria, M.5
Paredes, E.6
Vollhardt, K.P.C.7
-
57
-
-
33745728214
-
-
h) V. Gandon, N. Agenet, K. P. C. Vollhardt, M. Malacria, C. Aubert, J. Am. Chem. Soc. 2006, 128, 8509.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 8509
-
-
Gandon, V.1
Agenet, N.2
Vollhardt, K.P.C.3
Malacria, M.4
Aubert, C.5
-
58
-
-
34247882697
-
-
For selected examples of the Rh-catalyzed chelation-assisted intermolecular hydroarylation of alkynes and alkenes, see: a J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332;
-
For selected examples of the Rh-catalyzed chelation-assisted intermolecular hydroarylation of alkynes and alkenes, see: a) J. C. Lewis, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 5332;
-
-
-
-
59
-
-
0037127018
-
-
b) C.-H. Jun, C. W. Moon, J.-B. Hong, S.-G. Lim, K.-Y. Chung, Y.-H. Kim, Chem. Eur. J. 2002, 8, 485;
-
(2002)
Chem. Eur. J
, vol.8
, pp. 485
-
-
Jun, C.-H.1
Moon, C.W.2
Hong, J.-B.3
Lim, S.-G.4
Chung, K.-Y.5
Kim, Y.-H.6
-
61
-
-
0000961051
-
-
and references therein
-
d) U. R. Aulwurm, J. U. Melchinger, H. Kisch, Organometallics 1995, 14, 3385, and references therein.
-
(1995)
Organometallics
, vol.14
, pp. 3385
-
-
Aulwurm, U.R.1
Melchinger, J.U.2
Kisch, H.3
-
62
-
-
34547957272
-
-
I/(R)-binap catalyst was reported. However, the use of (R)-binap required the very slow addition (over a period of 30 min) of the enyne substrate; furthermore, neither the absolute configuration of the product nor electronic effects on the reaction were determined: K. Tsuchikama, Y. Kuwata, Y. Tahara, Y. Yoshinami, T. Shibata, Org. Lett. 2007, 9, 3097.
-
I/(R)-binap catalyst was reported. However, the use of (R)-binap required the very slow addition (over a period of 30 min) of the enyne substrate; furthermore, neither the absolute configuration of the product nor electronic effects on the reaction were determined: K. Tsuchikama, Y. Kuwata, Y. Tahara, Y. Yoshinami, T. Shibata, Org. Lett. 2007, 9, 3097.
-
-
-
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