-
1
-
-
0000134376
-
-
Hegedus, L. S, Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: Oxford, UK
-
(a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 741-770.
-
(1995)
Comprehensive Organometallic Chemistry II
, vol.12
, pp. 741-770
-
-
Grotjahn, D.B.1
-
2
-
-
0003779363
-
-
Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim, Germany
-
(b) Bonnemann, H.; Brijoux, W. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 171-197.
-
(2004)
Transition Metals for Organic Synthesis
, vol.1
, pp. 171-197
-
-
Bonnemann, H.1
Brijoux, W.2
-
6
-
-
75349103759
-
-
For rhenium-catalyzed reactions, see
-
For rhenium-catalyzed reactions, see:
-
-
-
-
7
-
-
26044451878
-
-
(a) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 13498
-
-
Kuninobu, Y.1
Kawata, A.2
Takai, K.3
-
8
-
-
38349170142
-
-
(b) Yudha, S. S.; Kuninobu, Y.; Takai, K. Org. Lett. 2007, 9, 5609.
-
(2007)
Org. Lett
, vol.9
, pp. 5609
-
-
Yudha, S.S.1
Kuninobu, Y.2
Takai, K.3
-
9
-
-
54949098548
-
-
(c) Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130, 14062.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 14062
-
-
Kuninobu, Y.1
Nishina, Y.2
Matsuki, T.3
Takai, K.4
-
10
-
-
56449124073
-
-
(d) Yudha, S. S.; Kuninobu, Y.; Takai, K. Angew. Chem., Int. Ed. 2008, 47, 9318.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 9318
-
-
Yudha, S.S.1
Kuninobu, Y.2
Takai, K.3
-
11
-
-
75349095819
-
-
For manganese-catalyzed reactions, see
-
For manganese-catalyzed reactions, see:
-
-
-
-
12
-
-
34548356420
-
-
(a) Kuninobu, Y.; Nishina, Y.; Takeuchi, T.; Takai, K. Angew. Chem., Int. Ed. 2007, 46, 6518.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 6518
-
-
Kuninobu, Y.1
Nishina, Y.2
Takeuchi, T.3
Takai, K.4
-
13
-
-
75349092434
-
-
Kuninobu, Y.; Kikuchi, K.; Takai, K. Chem. Lett. 2008, 37, 740. (5) Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823.
-
(b) Kuninobu, Y.; Kikuchi, K.; Takai, K. Chem. Lett. 2008, 37, 740. (5) Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823.
-
-
-
-
14
-
-
52049115226
-
-
Kuninobu, Y.; Nishi, M.; Yudha, S. S.; Takai, K. Org. Lett. 2008, 10, 3009.
-
(2008)
Org. Lett
, vol.10
, pp. 3009
-
-
Kuninobu, Y.1
Nishi, M.2
Yudha, S.S.3
Takai, K.4
-
15
-
-
45749106769
-
-
Another group also reported on the similar manganese-catalyzed reaction. See
-
Another group also reported on the similar manganese-catalyzed reaction. See: Tsuji, H.; Yamagata, K.-i.; Fujimoto, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 7792.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 7792
-
-
Tsuji, H.1
Yamagata, K.-I.2
Fujimoto, T.3
Nakamura, E.4
-
16
-
-
75349096412
-
-
When β-keto esters with a substituent at the active methylene moiety were used, insertion of alkynes into a carbon, carbon bond of β-keto esters occurred, and successive intramolecular cyclization gave 2-pyranones
-
When β-keto esters with a substituent at the active methylene moiety were used, insertion of alkynes into a carbon - carbon bond of β-keto esters occurred, and successive intramolecular cyclization gave 2-pyranones.
-
-
-
-
17
-
-
75349113728
-
-
See: Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, H.; Takai, K. Chem. Commun. 2008, 6360. (9) The intermediate shown in Scheme 2 is thought to be a manganese- and rhenium-catalyzed ring expansion and carbon-chain extension reaction. See: Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 11368. See also ref 8.
-
See: Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, H.; Takai, K. Chem. Commun. 2008, 6360. (9) The intermediate shown in Scheme 2 is thought to be a manganese- and rhenium-catalyzed ring expansion and carbon-chain extension reaction. See: Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 11368. See also ref 8.
-
-
-
-
18
-
-
67849111871
-
-
Nakamura's group reported on the mechanistic investigations. In the paper, they claimed that the reaction must proceed via the formation of alkenyl-magnesium intermediate (Scheme 3). See: Yoshikai, N.; Zhang, S.; Yamagata, K.-i.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 4099. (11) Kuninobu, Y.; Takata, H.; Kawata, A.; Takai, K. Org. Lett. 2008, 10, 3133.
-
Nakamura's group reported on the mechanistic investigations. In the paper, they claimed that the reaction must proceed via the formation of alkenyl-magnesium intermediate (Scheme 3). See: Yoshikai, N.; Zhang, S.; Yamagata, K.-i.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 4099. (11) Kuninobu, Y.; Takata, H.; Kawata, A.; Takai, K. Org. Lett. 2008, 10, 3133.
-
-
-
-
19
-
-
75349104228
-
-
For some representative examples of 2-pyranone synthesis, see
-
For some representative examples of 2-pyranone synthesis, see:
-
-
-
-
21
-
-
33845279846
-
-
(b) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140.
-
(1988)
J. Org. Chem
, vol.53
, pp. 3140
-
-
Tsuda, T.1
Morikawa, S.2
Sumiya, R.3
Saegusa, T.4
-
22
-
-
0032491016
-
-
(c) Larock, R. C.; Han, X.; Doty, M. J. Tetrahedron Lett. 1998, 39, 5713.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 5713
-
-
Larock, R.C.1
Han, X.2
Doty, M.J.3
-
23
-
-
33847789311
-
-
(d) Fukuyama, T.; Higashibeppu, Y.; Yamaura, R.; Ryu, I. Org. Lett. 2007, 9, 587.
-
(2007)
Org. Lett
, vol.9
, pp. 587
-
-
Fukuyama, T.1
Higashibeppu, Y.2
Yamaura, R.3
Ryu, I.4
-
24
-
-
0002338793
-
-
For the formation of aromatic compounds from 2-pyranones and acetylenes, see: a
-
For the formation of aromatic compounds from 2-pyranones and acetylenes, see: (a) Tam, T. F.; Coles, P. Synthesis 1988, 383.
-
(1988)
Synthesis
, pp. 383
-
-
Tam, T.F.1
Coles, P.2
-
25
-
-
0026730571
-
-
(b) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.
-
(1992)
Tetrahedron
, vol.48
, pp. 9111
-
-
Afarinkia, K.1
Vinader, V.2
Nelson, T.D.3
Posner, G.H.4
-
26
-
-
1842637760
-
-
Diels-Alder reactions between 2-pyranone 8b and alkyne 9a were investigated in the presence or absence of a rhenium catalyst, ReBr(CO)3(thf)]2, and MS4A to clarify the role of the rhenium catalyst and MS4A in the Diels-Alder reactions. The yields are as follows: no catalyst 53, ReBr(CO)3(thf)]2 (2.5 mol , 80, ReBr(CO)3(thf)]2 (2.5 mol , MS4A (200 wt%-Re cat, 64, and MS4A (200 wt%-Re cat, 40, These results show that a rhenium catalyst, ReBr(CO)3(thf)]2, accelerated the Diels-Alder reaction between 8b and 9a, whereas MS4A slightly inhibited the Diels-Alder reaction, 15) In the first step of the reaction, 2-pyranone 8b was formed in 96% yield, 16) For examples of transition metal-catalyzed Conia-ene reactions, see: (a) Kennedy-Smith, J. J, Staben, S. T, Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526
-
2, accelerated the Diels-Alder reaction between 8b and 9a, whereas MS4A slightly inhibited the Diels-Alder reaction. (15) In the first step of the reaction, 2-pyranone 8b was formed in 96% yield. (16) For examples of transition metal-catalyzed Conia-ene reactions, see: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
-
-
-
-
27
-
-
20444465253
-
-
(b) Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185.
-
(2005)
Org. Lett
, vol.7
, pp. 2185
-
-
Gao, Q.1
Zheng, B.-F.2
Li, J.-H.3
Yang, D.4
-
28
-
-
35648932005
-
-
(c) Tsuji, H.; Yamagata, K.-i.; Itoh, Y.; Endo, K.; Nakamura, M.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 8060.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 8060
-
-
Tsuji, H.1
Yamagata, K.-I.2
Itoh, Y.3
Endo, K.4
Nakamura, M.5
Nakamura, E.6
-
29
-
-
36849029796
-
-
Deng, C.-L.; Song, R.-J.; Guo, S.-M.; Wang, Z.-Q.; Li, J.-H. Org. Lett. 2007, 9, 5111. See also ref 5.
-
(d) Deng, C.-L.; Song, R.-J.; Guo, S.-M.; Wang, Z.-Q.; Li, J.-H. Org. Lett. 2007, 9, 5111. See also ref 5.
-
-
-
-
30
-
-
0002583629
-
-
There have been some examples on chemical transformations via carbon-carbon bond cleavage. See: a, Murai, S, Ed
-
There have been some examples on chemical transformations via carbon-carbon bond cleavage. See: (a) Murakami, M.; Ito, Y. (Murai, S., Ed.) Top. Organomet. Chem. 1999, 3, 97.
-
(1999)
Top. Organomet. Chem
, vol.3
, pp. 97
-
-
Murakami, M.1
Ito, Y.2
-
32
-
-
0010303901
-
-
(a) Kochetkov, N. K.; Kudryashov, L. J.; Gottich, B. P. Tetrahedron 1961, 12, 63.
-
(1961)
Tetrahedron
, vol.12
, pp. 63
-
-
Kochetkov, N.K.1
Kudryashov, L.J.2
Gottich, B.P.3
-
35
-
-
23044475190
-
-
Wiley, R. H.; Jarboe, C. H.; Hayes, F. N. J. Am. Chem. Soc. 1957, 79, 2602. (20) The structure of 17b was determined by the comparison with the spectrum data of 17b, which was prepared by palladium-catalyzed cross-coupling reaction between 4-methoxyphenylboronic acid and 2,3,5-trimethylphenyl trifluoromethanesulfonate.
-
(b) Wiley, R. H.; Jarboe, C. H.; Hayes, F. N. J. Am. Chem. Soc. 1957, 79, 2602. (20) The structure of 17b was determined by the comparison with the spectrum data of 17b, which was prepared by palladium-catalyzed cross-coupling reaction between 4-methoxyphenylboronic acid and 2,3,5-trimethylphenyl trifluoromethanesulfonate.
-
-
-
-
36
-
-
75349089936
-
-
In Scheme 5, the formation of β-keto acid was not detected by GC. The β-keto carboxylic acid might be decomposed (Krapcho reaction) or reacted with a species before decomposition under the reaction conditions. Therefore, the generation of β-keto carboxylic acid is only speculated.
-
In Scheme 5, the formation of β-keto acid was not detected by GC. The β-keto carboxylic acid might be decomposed (Krapcho reaction) or reacted with a species before decomposition under the reaction conditions. Therefore, the generation of β-keto carboxylic acid is only speculated.
-
-
-
|