-
1
-
-
79957725501
-
-
See, for example.
-
See, for example.
-
-
-
-
2
-
-
0034610759
-
-
A. Rossi, P. Kapahi, G. Natoli, T. Takahashi, Y. Chen, M. Karin, M. G. Santoro, Nature 2000, 403, 103-118;
-
(2000)
Nature
, vol.403
, pp. 103-118
-
-
Rossi, A.1
Kapahi, P.2
Natoli, G.3
Takahashi, T.4
Chen, Y.5
Karin, M.6
Santoro, M.G.7
-
5
-
-
40549125980
-
-
A. Ianaro, P. Maffia, M. D. Rosa, A. Ialenti, Curr. Med. Chem.: Anti-Inflammatory Anti-Allergy Agents 2003, 2, 85-93;
-
(2003)
Curr. Med. Chem.: Anti-Inflammatory Anti-Allergy Agents
, vol.2
, pp. 85-93
-
-
Ianaro, A.1
Maffia, P.2
Rosa, M.D.3
Ialenti, A.4
-
6
-
-
20444481934
-
-
A. Mithöfer, M. Maitrejean, W. Boland, J. Plant Growth Regul. 2004, 23, 170-178;
-
(2004)
J. Plant Growth Regul.
, vol.23
, pp. 170-178
-
-
Mithöfer, A.1
Maitrejean, M.2
Boland, W.3
-
9
-
-
79957751818
-
-
For recent examples, see.
-
For recent examples, see.
-
-
-
-
11
-
-
56949104328
-
-
Y. Fall, H. Doucet, M. Santelli, Tetrahedron 2009, 65, 489-495;
-
(2009)
Tetrahedron
, vol.65
, pp. 489-495
-
-
Fall, Y.1
Doucet, H.2
Santelli, M.3
-
12
-
-
61349179599
-
-
S. W. Kwok, J. E. Hein, V. V. Fokin, K. B. Sharpless, Heterocycles 2008, 76, 1141-1154;
-
(2008)
Heterocycles
, vol.76
, pp. 1141-1154
-
-
Kwok, S.W.1
Hein, J.E.2
Fokin, V.V.3
Sharpless, K.B.4
-
13
-
-
61349083074
-
-
H. P. Acharya, K. Miyoshi, Y. Takashima, N. Ogawa, Y. Kobayashi, Heterocycles 2008, 76, 1181-1189;
-
(2008)
Heterocycles
, vol.76
, pp. 1181-1189
-
-
Acharya, H.P.1
Miyoshi, K.2
Takashima, Y.3
Ogawa, N.4
Kobayashi, Y.5
-
14
-
-
44249097983
-
-
K. Takasu, K. Inanaga, M. Ihara, Tetrahedron Lett. 2008, 49, 4220-4222.
-
(2008)
Tetrahedron Lett.
, vol.49
, pp. 4220-4222
-
-
Takasu, K.1
Inanaga, K.2
Ihara, M.3
-
15
-
-
9944247495
-
-
and references therein.
-
S. E. Gibson, S. E. Lewis, N. Mainolfi, J. Organomet. Chem. 2004, 689, 3873-3890 and references therein.
-
(2004)
J. Organomet. Chem.
, vol.689
, pp. 3873-3890
-
-
Gibson, S.E.1
Lewis, S.E.2
Mainolfi, N.3
-
17
-
-
79957734007
-
-
For recent reviews on the Nazarov reaction, see.
-
For recent reviews on the Nazarov reaction, see.
-
-
-
-
18
-
-
0001992172
-
-
K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. 1994, 45, 1-158;
-
(1994)
Org. React.
, vol.45
, pp. 1-158
-
-
Habermas, K.L.1
Denmark, S.E.2
Jones, T.K.3
-
23
-
-
63149143373
-
-
S. Gao, Q. Wang, C. Chen, J. Am. Chem. Soc. 2009, 131, 1410-1412;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 1410-1412
-
-
Gao, S.1
Wang, Q.2
Chen, C.3
-
24
-
-
38349004628
-
-
W. He, J. Huang, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2008, 130, 300-308;
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 300-308
-
-
He, W.1
Huang, J.2
Sun, X.3
Frontier, A.J.4
-
26
-
-
55049088930
-
-
D. R. Williams, L. A. Robinson, C. R. Nevill, J. P. Reddy, Angew. Chem. 2007, 119, 933-936
-
(2007)
Angew. Chem.
, vol.119
, pp. 933-936
-
-
Williams, D.R.1
Robinson, L.A.2
Nevill, C.R.3
Reddy, J.P.4
-
27
-
-
33846699839
-
-
D. R. Williams, L. A. Robinson, C. R. Nevill, J. P. Reddy, Angew. Chem. Int. Ed. 2007, 46, 915-918.
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 915-918
-
-
Williams, D.R.1
Robinson, L.A.2
Nevill, C.R.3
Reddy, J.P.4
-
28
-
-
62049085602
-
-
D. P. Canterbury, I. R. Herrick, J. Um, K. N. Houk, A. J. Frontier, Tetrahedron 2009, 65, 3165-3179.
-
(2009)
Tetrahedron
, vol.65
, pp. 3165-3179
-
-
Canterbury, D.P.1
Herrick, I.R.2
Um, J.3
Houk, K.N.4
Frontier, A.J.5
-
29
-
-
11144277521
-
-
V. Cadierno, J. Díez, S. E. García-Garrido, J. Gimeno, Chem. Commun. 2004, 2716-2717.
-
(2004)
Chem. Commun.
, pp. 2716-2717
-
-
Cadierno, V.1
Díez, J.2
García-Garrido, S.E.3
Gimeno, J.4
-
30
-
-
79957758551
-
-
Reported examples include: a) Meyer-Schuster and Rupe-type rearrangements to afford α,β-unsaturated carbonyl compounds; b) C-C couplings of tertiary alkynols with enolizable ketones to generate conjugated dienones or diene-diones; c) furan, pyran, or pyrrole ring- formation reactions by cyclizative coupling of secondary propargylic alcohols with 1,3-dicarbonyl compounds and primary amines. See.
-
Reported examples include: a) Meyer-Schuster and Rupe-type rearrangements to afford α, β-unsaturated carbonyl compounds; b) C-C couplings of tertiary alkynols with enolizable ketones to generate conjugated dienones or diene-diones; c) furan, pyran, or pyrrole ring- formation reactions by cyclizative coupling of secondary propargylic alcohols with 1, 3-dicarbonyl compounds and primary amines. See.
-
-
-
-
31
-
-
31544473149
-
-
V. Cadierno, S. E. García-Garrido, J. Gimeno, Adv. Synth. Catal. 2006, 348, 101-110;
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 101-110
-
-
Cadierno, V.1
García-Garrido, S.E.2
Gimeno, J.3
-
32
-
-
33750524263
-
-
V. Cadierno, J. Díez, S. E. García-Garrido, J. Gimeno, N. Nebra, Adv. Synth. Catal. 2006, 348, 2125-2132;
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 2125-2132
-
-
Cadierno, V.1
Díez, J.2
García-Garrido, S.E.3
Gimeno, J.4
Nebra, N.5
-
33
-
-
34547168331
-
-
V. Cadierno, J. Gimeno, N. Nebra, Adv. Synth. Catal. 2007, 349, 382-394;
-
(2007)
Adv. Synth. Catal.
, vol.349
, pp. 382-394
-
-
Cadierno, V.1
Gimeno, J.2
Nebra, N.3
-
34
-
-
37249029243
-
-
V. Cadierno, J. Gimeno, N. Nebra, Chem. Eur. J. 2007, 13, 9973-9981;
-
(2007)
Chem. Eur. J.
, vol.13
, pp. 9973-9981
-
-
Cadierno, V.1
Gimeno, J.2
Nebra, N.3
-
35
-
-
48249141067
-
-
V. Cadierno, J. Díez, J. Gimeno, N. Nebra, J. Org. Chem. 2008, 73, 5852-5858;
-
(2008)
J. Org. Chem.
, vol.73
, pp. 5852-5858
-
-
Cadierno, V.1
Díez, J.2
Gimeno, J.3
Nebra, N.4
-
36
-
-
76149121537
-
-
V. Cadierno, J. Gimeno, N. Nebra, J. Heterocycl. Chem. 2010, 47, 233-236.
-
(2010)
J. Heterocycl. Chem.
, vol.47
, pp. 233-236
-
-
Cadierno, V.1
Gimeno, J.2
Nebra, N.3
-
38
-
-
79957704836
-
-
Nazarov-type cyclizations by coupling of enolizable vinyl ketones and aldehydes have been described. See, for example.
-
Nazarov-type cyclizations by coupling of enolizable vinyl ketones and aldehydes have been described. See, for example.
-
-
-
-
39
-
-
0032907450
-
-
T. Kajioka, M. Oda, S. Yamada, Y. Kawamori, R. Miyatake, S. Kuroda, Synthesis 1999, 184-187;
-
(1999)
Synthesis
, pp. 184-187
-
-
Kajioka, T.1
Oda, M.2
Yamada, S.3
Kawamori, Y.4
Miyatake, R.5
Kuroda, S.6
-
40
-
-
0032871009
-
-
M. Oda, T. Kajioka, K. Haramoto, R. Miyatake, S. Kuroda, Synthesis 1999, 1349-1353.
-
(1999)
Synthesis
, pp. 1349-1353
-
-
Oda, M.1
Kajioka, T.2
Haramoto, K.3
Miyatake, R.4
Kuroda, S.5
-
41
-
-
79957679702
-
-
To our knowledge, the involvement of propargylic alcohols in intermolecular one-pot Nazarov-type processes is unprecedented. Only two-step intermolecular cyclopentannulation reactions, by coupling of cycloalkanones and acyclic propargylic alcohols, have been described. They involve the initial addition of the dilithium salt of the alkynol to the carbonyl compound and a subsequent acid-catalyzed Rupe/Nazarov sequence. See, for example.
-
To our knowledge, the involvement of propargylic alcohols in intermolecular one-pot Nazarov-type processes is unprecedented. Only two-step intermolecular cyclopentannulation reactions, by coupling of cycloalkanones and acyclic propargylic alcohols, have been described. They involve the initial addition of the dilithium salt of the alkynol to the carbonyl compound and a subsequent acid-catalyzed Rupe/Nazarov sequence. See, for example.
-
-
-
-
42
-
-
37049135510
-
-
G. A. Mac Alpine, R. A. Raphael, A. Shaw, A. W. Taylor, H.-J. Wild, J. Chem. Soc. Chem. Commun. 1974, 834-835;
-
(1974)
J. Chem. Soc. Chem. Commun.
, pp. 834-835
-
-
MacAlpine, G.A.1
Raphael, R.A.2
Shaw, A.3
Taylor, A.W.4
Wild, H.-J.5
-
43
-
-
0001360107
-
-
T. Hiyama, M. Shinoda, H. Nozaki, J. Am. Chem. Soc. 1979, 101, 1599-1600;
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 1599-1600
-
-
Hiyama, T.1
Shinoda, M.2
Nozaki, H.3
-
44
-
-
0007616262
-
-
Some multistep intramolecular examples are also known. See, for example.
-
T. Hiyama, M. Shinoda, H. Saimoto, H. Nozaki, Bull. Chem. Soc. Jpn. 1981, 54, 2747-2758. Some multistep intramolecular examples are also known. See, for example.
-
(1981)
Bull. Chem. Soc. Jpn.
, vol.54
, pp. 2747-2758
-
-
Hiyama, T.1
Shinoda, M.2
Saimoto, H.3
Nozaki, H.4
-
45
-
-
0028131538
-
-
P. A. Jacobi, L. M. Armacost, H. L. Brielmann, R. O. Cann, J. I. Kravitz, M. J. Martinelli, J. Org. Chem. 1994, 59, 5292-5304;
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5292-5304
-
-
Jacobi, P.A.1
Armacost, L.M.2
Brielmann, H.L.3
Cann, R.O.4
Kravitz, J.I.5
Martinelli, M.J.6
-
46
-
-
0000589215
-
-
W. Baidossi, M. Lahav, J. Blum, J. Org. Chem. 1997, 62, 669-672;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 669-672
-
-
Baidossi, W.1
Lahav, M.2
Blum, J.3
-
48
-
-
79957680954
-
-
In the absence of the precatalyst 1, cyclopentenone 3a is formed in only 15% yield after 24 h at 75°C;
-
In the absence of the precatalyst 1, cyclopentenone 3a is formed in only 15% yield after 24 h at 75°C;
-
-
-
-
49
-
-
79957727994
-
-
The coupling of the independently synthesized enone 1-acetylcyclooctene with benzaldehyde has also been studied. In the absence of TFA, complex 1 by itself (5 mol%) was not able to promote the formation of 3a, even after 24 h at 75°C. Under the same reaction conditions, the use of TFA (50 mol%) in the absence of complex 1 led to 3a in only 29% GC yield after 24 h. In contrast, the combined use of 1 (5 mol%) and TFA (50 mol%) afforded 3a in high yield (93% by GC) after 10 h of heating. These results clearly indicate the active role of the Lewis acid-ruthenium species in the reaction sequence.
-
The coupling of the independently synthesized enone 1-acetylcyclooctene with benzaldehyde has also been studied. In the absence of TFA, complex 1 by itself (5 mol%) was not able to promote the formation of 3a, even after 24 h at 75°C. Under the same reaction conditions, the use of TFA (50 mol%) in the absence of complex 1 led to 3a in only 29% GC yield after 24 h. In contrast, the combined use of 1 (5 mol%) and TFA (50 mol%) afforded 3a in high yield (93% by GC) after 10 h of heating. These results clearly indicate the active role of the Lewis acid-ruthenium species in the reaction sequence.
-
-
-
-
50
-
-
79957692583
-
-
The preparation of compounds 3a and 3l through alternative routes has been described.
-
The preparation of compounds 3a and 3l through alternative routes has been described.
-
-
-
-
52
-
-
50549208417
-
-
R. Breslow, W. Vitale, K. Wendel, Tetrahedron Lett. 1965, 6, 365-368.
-
(1965)
Tetrahedron Lett.
, vol.6
, pp. 365-368
-
-
Breslow, R.1
Vitale, W.2
Wendel, K.3
-
53
-
-
79957744913
-
-
The intermediate formation of 4 was confirmed by monitoring the catalytic reaction by GC/MS;
-
The intermediate formation of 4 was confirmed by monitoring the catalytic reaction by GC/MS;
-
-
-
-
54
-
-
0000894377
-
-
Rupe-type rearrangements proceed through the initial dehydration of the propargylic alcohol, followed by hydration of the C≡C bond of the resulting enyne. For a review on the Rupe reaction, see
-
Rupe-type rearrangements proceed through the initial dehydration of the propargylic alcohol, followed by hydration of the C≡C bond of the resulting enyne. For a review on the Rupe reaction, see: S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429-438.
-
(1971)
Chem. Rev.
, vol.71
, pp. 429-438
-
-
Swaminathan, S.1
Narayanan, K.V.2
-
55
-
-
79957669800
-
-
Metal-catalyzed addition of carboxylic acids to terminal alkynes is a well-known process, with ruthenium catalysts playing a prominent role. For reviews, see.
-
Metal-catalyzed addition of carboxylic acids to terminal alkynes is a well-known process, with ruthenium catalysts playing a prominent role. For reviews, see.
-
-
-
-
56
-
-
4444376920
-
-
F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3160;
-
(2004)
Chem. Rev.
, vol.104
, pp. 3079-3160
-
-
Alonso, F.1
Beletskaya, I.P.2
Yus, M.3
-
57
-
-
20444478248
-
-
in (Ed.: S.-I. Murahashi), Wiley-VCH, Weinheim, For specific examples of ruthenium-catalyzed Markovnikov addition of carboxylic acids to 1,3-enynes, see.
-
C. Fischmeister, C. Bruneau, P. H. Dixneuf in Ruthenium in Organic Synthesis (Ed.: S.-I. Murahashi), Wiley-VCH, Weinheim, 2004, pp. 189-217. For specific examples of ruthenium-catalyzed Markovnikov addition of carboxylic acids to 1, 3-enynes, see.
-
(2004)
Ruthenium in Organic Synthesis
, pp. 189-217
-
-
Fischmeister, C.1
Bruneau, C.2
Dixneuf, P.H.3
-
59
-
-
0001357269
-
-
M. Neveux, B. Seiller, F. Hagedorn, C. Bruneau, P. H. Dixneuf, J. Organomet. Chem. 1993, 451, 133-138.
-
(1993)
J. Organomet. Chem.
, vol.451
, pp. 133-138
-
-
Neveux, M.1
Seiller, B.2
Hagedorn, F.3
Bruneau, C.4
Dixneuf, P.H.5
-
60
-
-
79957786265
-
-
In the absence of directing functional groups, the generation of fused cyclopentenone rings through Nazarov-type processes usually proceeds without control of the ring-fusion stereochemistry. See, for example.
-
In the absence of directing functional groups, the generation of fused cyclopentenone rings through Nazarov-type processes usually proceeds without control of the ring-fusion stereochemistry. See, for example.
-
-
-
-
61
-
-
0004983905
-
-
W. E. Fristad, D. S. Dime, T. R. Bailey, L. A. Paquette, Tetrahedron Lett. 1979, 20, 1999-2002;
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 1999-2002
-
-
Fristad, W.E.1
Dime, D.S.2
Bailey, T.R.3
Paquette, L.A.4
-
62
-
-
33847087629
-
-
L. A. Paquette, W. E. Fristad, D. S. Dime, T. R. Bailey, J. Org. Chem. 1980, 45, 3017-3028;
-
(1980)
J. Org. Chem.
, vol.45
, pp. 3017-3028
-
-
Paquette, L.A.1
Fristad, W.E.2
Dime, D.S.3
Bailey, T.R.4
-
64
-
-
79957671048
-
-
Formation of 8b and 9b through an acid- or metal-catalyzed isomerization of the C=C bond in 8a and 9a has been ruled out. Isolated compounds 8a and 9a remained unchanged when treated with 1/TFA for 24 h at 75°C.
-
Formation of 8b and 9b through an acid- or metal-catalyzed isomerization of the C=C bond in 8a and 9a has been ruled out. Isolated compounds 8a and 9a remained unchanged when treated with 1/TFA for 24 h at 75°C.
-
-
-
|