-
2
-
-
0036522941
-
-
b) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
-
(2002)
Chem. Rev
, vol.102
, pp. 813-834
-
-
Aubert, C.1
Buisine, O.2
Malacria, M.3
-
6
-
-
27744492121
-
-
f) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
-
(2005)
Angew. Chem
, vol.117
, pp. 2380-2386
-
-
Bruneau, C.1
-
7
-
-
18044386806
-
-
Angew. Chem. Int. Ed. 2005, 44, 2328-2334;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 2328-2334
-
-
-
8
-
-
33746305520
-
-
g) S. Ma, S. Yu, Z. Gu, Angew. Chem. 2006, 118, 206-209;
-
(2006)
Angew. Chem
, vol.118
, pp. 206-209
-
-
Ma, S.1
Yu, S.2
Gu, Z.3
-
9
-
-
33745446200
-
-
Angew. Chem. Int. Ed. 2006, 45, 200-203;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 200-203
-
-
-
10
-
-
33747175365
-
-
h) C. Nieto-Oberhuber, S. Lopez, E. Jiménez-Nüñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 5916-5923
-
-
Nieto-Oberhuber, C.1
Lopez, S.2
Jiménez-Nüñez, E.3
Echavarren, A.M.4
-
12
-
-
34250824768
-
-
Angew. Chem. Int. Ed. 2007, 46, 3410-3449.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 3410-3449
-
-
-
14
-
-
36749027602
-
-
Angew. Chem. Int. Ed. 2007, 46, 8845-8849.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 8845-8849
-
-
-
15
-
-
53549098912
-
-
S. M. Kim, J. H. Park, S. Y. Choi, Y. K. Chung Angew. Chem. 2007, 119, 6284-6287;
-
(2007)
Angew. Chem
, vol.119
, pp. 6284-6287
-
-
Kim, S.M.1
Park, J.H.2
Choi, S.Y.3
Chung, Y.K.4
-
16
-
-
34548085645
-
-
Angew. Chem. Int. Ed. 2007, 46, 6172-6175;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 6172-6175
-
-
-
17
-
-
34548085645
-
-
Angew. Chem. Int. Ed. 2007, 46, 6172-6175.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 6172-6175
-
-
-
18
-
-
0032500353
-
-
For examples in which vicinal biscyclopropanes were formed by the cycloisomerization of dienynes, see a
-
For examples in which vicinal biscyclopropanes were formed by the cycloisomerization of dienynes, see a) Ru: N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105;
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 9104-9105
-
-
Ru, N.1
Chatani, K.2
Kataoka, S.3
Murai, N.4
Furukawa, Y.S.5
-
20
-
-
53549129316
-
-
Pt: c E. Mainetti, V. Mouries, L. Fensterbank, M. Malacria, J. Marco-Contelles, Angew. Chem. 2002, 114, 2236-2239;
-
Pt: c) E. Mainetti, V. Mouries, L. Fensterbank, M. Malacria, J. Marco-Contelles, Angew. Chem. 2002, 114, 2236-2239;
-
-
-
-
21
-
-
0037124890
-
-
Angew. Chem. Int. Ed. 2002, 41, 2132-2135;
-
(2002)
Angew. Chem. Int. Ed
, vol.41
, pp. 2132-2135
-
-
-
22
-
-
33750402116
-
-
d) J. Marco-Contelles, N. Arroyo, S. Anjum, E. Mainetti, N. Marion, K. Cariou, G. Lemière, V. Mouries, L. Fensterbank, M. Malacria, Eur. J. Org. Chem. 2006, 4618-4633;
-
(2006)
Eur. J. Org. Chem
, pp. 4618-4633
-
-
Marco-Contelles, J.1
Arroyo, N.2
Anjum, S.3
Mainetti, E.4
Marion, N.5
Cariou, K.6
Lemière, G.7
Mouries, V.8
Fensterbank, L.9
Malacria, M.10
-
23
-
-
53549105890
-
-
Au: e C. Nieto-Oberhuber, M. Paz Muñoz, E. Bunuel, C. Nevado, D. J. Cardenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
-
Au: e) C. Nieto-Oberhuber, M. Paz Muñoz, E. Bunuel, C. Nevado, D. J. Cardenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
-
-
-
-
24
-
-
3242741475
-
-
Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 2402-2406
-
-
-
25
-
-
32944466105
-
-
f) C. Nieto-Oberhuber, S. Lopez, M. Paz Muñoz, E. Jimenez-Nunez, E. Bunuel, D. J. Cardenas, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1694-1702.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 1694-1702
-
-
Nieto-Oberhuber, C.1
Lopez, S.2
Paz Muñoz, M.3
Jimenez-Nunez, E.4
Bunuel, E.5
Cardenas, D.J.6
Echavarren, A.M.7
-
26
-
-
0034637490
-
-
a) N. Chatani, H. Inoue, T. Ikeda, S. Murai, J. Org. Chem. 2000, 65, 4913-4918;
-
(2000)
J. Org. Chem
, vol.65
, pp. 4913-4918
-
-
Chatani, N.1
Inoue, H.2
Ikeda, T.3
Murai, S.4
-
27
-
-
0037154820
-
-
b) H. Inoue, N. Chatani, S. Murai, J. Org. Chem. 2002, 67, 1414-1417;
-
(2002)
J. Org. Chem
, vol.67
, pp. 1414-1417
-
-
Inoue, H.1
Chatani, N.2
Murai, S.3
-
29
-
-
0042152109
-
-
d) S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055-1058;
-
(2003)
Org. Lett
, vol.5
, pp. 1055-1058
-
-
Pastine, S.J.1
Youn, S.W.2
Sames, D.3
-
31
-
-
0037620537
-
-
f) B. Martin-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757-5766;
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 5757-5766
-
-
Martin-Matute, B.1
Nevado, C.2
Cárdenas, D.J.3
Echavarren, A.M.4
-
32
-
-
0142248466
-
-
g) S. J. Pastine, S. W. Youn, D. Sames, Tetrahedron 2003, 59, 8859-8868;
-
(2003)
Tetrahedron
, vol.59
, pp. 8859-8868
-
-
Pastine, S.J.1
Youn, S.W.2
Sames, D.3
-
33
-
-
4744342870
-
-
h) V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575;
-
(2004)
Chem. Eur. J
, vol.10
, pp. 4556-4575
-
-
Mamane, V.1
Hannen, P.2
Fürstner, A.3
-
34
-
-
18244388692
-
-
i) Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B. W. Slafer, A. Davis, Org. Lett. 2005, 7, 1047-1050;
-
(2005)
Org. Lett
, vol.7
, pp. 1047-1050
-
-
Zhang, Y.1
Hsung, R.P.2
Zhang, X.3
Huang, J.4
Slafer, B.W.5
Davis, A.6
-
37
-
-
33746081826
-
-
Angew. Chem. Int. Ed. 2006, 45, 1105-1109.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 1105-1109
-
-
-
38
-
-
20544468222
-
-
M. Achard, A. Tenaglia, G. Buono, Org. Lett. 2005, 7, 2353-2356.
-
(2005)
Org. Lett
, vol.7
, pp. 2353-2356
-
-
Achard, M.1
Tenaglia, A.2
Buono, G.3
-
39
-
-
53549085214
-
-
13C NMR spectroscopy and by comparison with the NMR data of similar compounds; see Ref. [7] and [9].
-
13C NMR spectroscopy and by comparison with the NMR data of similar compounds; see Ref. [7] and [9].
-
-
-
-
40
-
-
0013519346
-
-
J. H. Rigby, M. Kirova, N. Niyaz, F. Mohammadi, Synlett 1997, 805-806.
-
(1997)
Synlett
, pp. 805-806
-
-
Rigby, J.H.1
Kirova, M.2
Niyaz, N.3
Mohammadi, F.4
-
41
-
-
0035980290
-
-
M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10 511-10520.
-
(2001)
J. Am. Chem. Soc
, vol.123
, Issue.10
, pp. 511-10520
-
-
Méndez, M.1
Muñoz, M.P.2
Nevado, C.3
Cárdenas, D.J.4
Echavarren, A.M.5
-
42
-
-
0001698888
-
-
2, see a) N. Chatani, T. Morimoto, T. Muto, S. Murai, J. Am. Chem. Soc. 1994, 116, 6049-6050;
-
2, see a) N. Chatani, T. Morimoto, T. Muto, S. Murai, J. Am. Chem. Soc. 1994, 116, 6049-6050;
-
-
-
-
43
-
-
0001525502
-
-
b) N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901-903.
-
(1996)
Organometallics
, vol.15
, pp. 901-903
-
-
Chatani, N.1
Furukawa, N.2
Sakurai, H.3
Murai, S.4
-
44
-
-
15944427478
-
-
2, see M. P. Muñoz, J. Adrio, J. A. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
-
2, see M. P. Muñoz, J. Adrio, J. A. Carretero, A. M. Echavarren, Organometallics 2005, 24, 1293-1300.
-
-
-
-
47
-
-
53549108119
-
-
A single-crystal X-ray analysis of cycloadduct 2c secured the tricyclic structure of the adduct. CCDC 655906 contains 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.
-
A single-crystal X-ray analysis of cycloadduct 2c secured the tricyclic structure of the adduct. CCDC 655906 contains 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.
-
-
-
-
48
-
-
0035921537
-
-
S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709.
-
(2001)
Organometallics
, vol.20
, pp. 3704-3709
-
-
Oi, S.1
Tsukamoto, I.2
Miyano, S.3
Inoue, Y.4
-
49
-
-
20444496467
-
-
The strong π-acid character of this ligand, which increases the electrophilicity of the metal center while being sufficiently labile, has been exploited in some platinum-catalyzed cycloisomerizations: a A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245;
-
The strong π-acid character of this ligand, which increases the electrophilicity of the metal center while being sufficiently labile, has been exploited in some platinum-catalyzed cycloisomerizations: a) A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245;
-
-
-
-
52
-
-
0038081446
-
-
a) A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785-6786;
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 6785-6786
-
-
Fürstner, A.1
Szillat, H.2
Stelzer, F.3
-
53
-
-
0035814401
-
-
b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11 863-11869.
-
(2001)
J. Am. Chem. Soc
, vol.123
, Issue.11
, pp. 863-11869
-
-
Fürstner, A.1
Stelzer, F.2
Szillat, H.3
-
54
-
-
33746651540
-
-
For recent examples of 1,2-shifts in carbenoids, see a
-
For recent examples of 1,2-shifts in carbenoids, see a) J. Sun, M. P. Conley, L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705-9710;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9705-9710
-
-
Sun, J.1
Conley, M.P.2
Zhang, L.3
Kozmin, S.A.4
-
55
-
-
31544464934
-
-
b) H. Kusama, Y. Miyashita, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 289-292;
-
(2006)
Org. Lett
, vol.8
, pp. 289-292
-
-
Kusama, H.1
Miyashita, Y.2
Takaya, J.3
Iwasawa, N.4
-
56
-
-
33746364845
-
-
and references therein;
-
c) F. Xiao, J. Wang, J. Org. Chem. 2006, 71, 5789-5791, and references therein;
-
(2006)
J. Org. Chem
, vol.71
, pp. 5789-5791
-
-
Xiao, F.1
Wang, J.2
-
57
-
-
38049033193
-
-
d) H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927-929;
-
(2007)
Angew. Chem
, vol.119
, pp. 927-929
-
-
Funami, H.1
Kusama, H.2
Iwasawa, N.3
-
58
-
-
33846670579
-
-
Angew. Chem. Int. Ed. 2007, 46, 909-911;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 909-911
-
-
-
60
-
-
33846675942
-
-
Angew. Chem. Int. Ed. 2007, 46, 912-914;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 912-914
-
-
-
61
-
-
33947607969
-
-
f) C. R. Smith, E. M. Bunnelle, A. J. Rhodes, R. Sarpong, Org. Lett. 2007, 9, 1169-1171;
-
(2007)
Org. Lett
, vol.9
, pp. 1169-1171
-
-
Smith, C.R.1
Bunnelle, E.M.2
Rhodes, A.J.3
Sarpong, R.4
-
63
-
-
34447342869
-
-
Angew. Chem. Int. Ed. 2007, 46, 5195-5197.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 5195-5197
-
-
-
64
-
-
53549125341
-
-
Attempts to convert tricyclic ether 7e into bicyclic alcohol 11 resulted in the same observations.
-
Attempts to convert tricyclic ether 7e into bicyclic alcohol 11 resulted in the same observations.
-
-
-
-
65
-
-
53549121244
-
-
Subjecting a mixture of 8b and 9b (1:1.7; Table 3, entry 2) to the same conditions resulted in total consumption of 8b but the reaction suffered from substantial degradation of the starting materials.
-
Subjecting a mixture of 8b and 9b (1:1.7; Table 3, entry 2) to the same conditions resulted in total consumption of 8b but the reaction suffered from substantial degradation of the starting materials.
-
-
-
-
66
-
-
53549126709
-
-
We warmly thank one reviewer for helpful comments
-
We warmly thank one reviewer for helpful comments.
-
-
-
-
67
-
-
34248597739
-
-
2SO or cyclopropanation of norbornene were unsuccessful and afforded exclusively 2a in excellent yields; a C. A. Witham, P. Mauleon, N. D. Shapiro, B. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 5838-5839;
-
2SO or cyclopropanation of norbornene were unsuccessful and afforded exclusively 2a in excellent yields; a) C. A. Witham, P. Mauleon, N. D. Shapiro, B. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 5838-5839;
-
-
-
-
68
-
-
33845772273
-
-
b) S. López, E. Herrero-Gomez, P. Pérez-Galan, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 6175-6178;
-
(2006)
Angew. Chem
, vol.118
, pp. 6175-6178
-
-
López, S.1
Herrero-Gomez, E.2
Pérez-Galan, P.3
Nieto-Oberhuber, C.4
Echavarren, A.M.5
-
69
-
-
33748792796
-
-
Angew. Chem. Int. Ed. 2006, 45, 6029-6032.
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 6029-6032
-
-
-
70
-
-
53549095782
-
-
To test this assumption, we attempted to trap the stabilized cation with nucleophilic species. Indeed, treatment of 7 f with boron trifluoride and triethylsilane afforded 12 (51%), by reductive ring cleavage, and oxatriquinane 13 (24%), by isomerization through participation of the phenyl substituent. See the Supporting Information.. (Chemical Equation Presented).
-
To test this assumption, we attempted to trap the stabilized cation with nucleophilic species. Indeed, treatment of 7 f with boron trifluoride and triethylsilane afforded 12 (51%), by reductive ring cleavage, and oxatriquinane 13 (24%), by isomerization through participation of the phenyl substituent. See the Supporting Information.. (Chemical Equation Presented).
-
-
-
|