-
2
-
-
51049121927
-
-
b) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
-
(2008)
Chem. Rev
, vol.108
, pp. 3239
-
-
Li, Z.1
Brouwer, C.2
He, C.3
-
8
-
-
0002110351
-
-
f) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49.
-
(1996)
Chem. Rev
, vol.96
, pp. 49
-
-
Lautens, M.1
Klute, W.2
Tam, W.3
-
9
-
-
69049113944
-
-
For gold-catalyzed intermolecular cycloaddition reactions, see: a
-
For gold-catalyzed intermolecular cycloaddition reactions, see: a) N. D. Shapiro; Y. Shi, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 11654;
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 11654
-
-
Shapiro, N.D.1
Shi, Y.2
Toste, F.D.3
-
11
-
-
59649102559
-
-
b) S. Suárez-Pantiga, E. Rubio, C. Alvarez-Rúa, J. M. González, Org. Lett. 2009, 11, 13;
-
(2009)
Org. Lett
, vol.11
, pp. 13
-
-
Suárez-Pantiga, S.1
Rubio, E.2
Alvarez-Rúa, C.3
González, J.M.4
-
14
-
-
44449159964
-
-
e) G. Li, X. Huang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 6944;
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 6944
-
-
Li, G.1
Huang, X.2
Zhang, L.3
-
15
-
-
39049105773
-
-
f) G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814;
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 1814
-
-
Zhang, G.1
Huang, X.2
Li, G.3
Zhang, L.4
-
16
-
-
70349299260
-
-
g) F. Liu, Y. Yu, J. Zhang, Angew. Chem. 2008, 120, 5613;
-
(2008)
Angew. Chem
, vol.120
, pp. 5613
-
-
Liu, F.1
Yu, Y.2
Zhang, J.3
-
19
-
-
54749142526
-
-
i) M. Schelwies, A. L. Dempwolff, F. Rominger, G. Helmchen, Angew. Chem. 2007, 119, 5694;
-
(2007)
Angew. Chem
, vol.119
, pp. 5694
-
-
Schelwies, M.1
Dempwolff, A.L.2
Rominger, F.3
Helmchen, G.4
-
21
-
-
38949204035
-
-
j) Y.-C. Hsu, S. Datta, C.-M. Ting, R.-S. Liu, Org. Lett. 2008, 10, 521;
-
(2008)
Org. Lett
, vol.10
, pp. 521
-
-
Hsu, Y.-C.1
Datta, S.2
Ting, C.-M.3
Liu, R.-S.4
-
22
-
-
57149091342
-
-
k) C. C. Lin, T.-M. Teng, C. C. Tsai, H.-Y. Liao, R. S. Liu, J. Am. Chem. Soc. 2008, 130, 16417.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 16417
-
-
Lin, C.C.1
Teng, T.-M.2
Tsai, C.C.3
Liao, H.-Y.4
Liu, R.S.5
-
23
-
-
67949104905
-
-
For cycloadditions of 2-oxyallyl cations, see selected examples: a
-
For cycloadditions of 2-oxyallyl cations, see selected examples: a) W. K. Chung, S. K. Lam, B. Lo, L. L. Liu, W.-T. Wong, P. Chiu, J. Am. Chem. Soc. 2009, 131, 4556;
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 4556
-
-
Chung, W.K.1
Lam, S.K.2
Lo, B.3
Liu, L.L.4
Wong, W.-T.5
Chiu, P.6
-
24
-
-
0142135994
-
-
b) H. Xiong, J. Huang, S. K. Ghosh, R. P. Hsung, J. Am. Chem. Soc. 2003, 125, 12694;
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 12694
-
-
Xiong, H.1
Huang, J.2
Ghosh, S.K.3
Hsung, R.P.4
-
26
-
-
0033518564
-
-
d) Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876;
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 876
-
-
Wang, Y.1
Arif, A.M.2
West, F.G.3
-
27
-
-
0000078752
-
-
e) M. Ohno, K. Mori, T. Hattori, S. Eguchi, J. Org. Chem. 1990, 55, 6086.
-
(1990)
J. Org. Chem
, vol.55
, pp. 6086
-
-
Ohno, M.1
Mori, K.2
Hattori, T.3
Eguchi, S.4
-
28
-
-
0000456845
-
-
Cycloaddition of 1-oxyallyl cations is only operable with dienes, see a P. G. Gassman, D. A. Singleton, J. Org. Chem. 1986, 51, 3075;
-
Cycloaddition of 1-oxyallyl cations is only operable with dienes, see a) P. G. Gassman, D. A. Singleton, J. Org. Chem. 1986, 51, 3075;
-
-
-
-
29
-
-
0000488506
-
-
b) P. G. Gassman, D. A. Singleton, J. J. Wilwerding, S. P. Chavan, J. Am. Chem. Soc. 1987, 109, 2183;
-
(1987)
J. Am. Chem. Soc
, vol.109
, pp. 2183
-
-
Gassman, P.G.1
Singleton, D.A.2
Wilwerding, J.J.3
Chavan, S.P.4
-
32
-
-
3042776636
-
-
a) R. J. Madhushaw, M.-Y. Lin, S. M. A. Sohel, R.-S. Liu, J. Am. Chem. Soc. 2004, 126, 6895;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 6895
-
-
Madhushaw, R.J.1
Lin, M.-Y.2
Sohel, S.M.A.3
Liu, R.-S.4
-
33
-
-
60949087960
-
-
b) G.-Y. Lin, C.-W. Li, S.-H. Hung, R.-S. Liu, Org. Lett. 2008, 10, 5059.
-
(2008)
Org. Lett
, vol.10
, pp. 5059
-
-
Lin, G.-Y.1
Li, C.-W.2
Hung, S.-H.3
Liu, R.-S.4
-
35
-
-
60949090068
-
-
b) C. M. Marson, A. Khan, J. McGregor, Tetrahedron Lett. 1995, 36, 7154;
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 7154
-
-
Marson, C.M.1
Khan, A.2
McGregor, J.3
-
36
-
-
0003207771
-
-
c) A. Gansäuer, M. Pierobon, H. Bluhm, Angew. Chem. 1998, 110, 107;
-
(1998)
Angew. Chem
, vol.110
, pp. 107
-
-
Gansäuer, A.1
Pierobon, M.2
Bluhm, H.3
-
38
-
-
0032539234
-
-
d) A. Gansäuer, H. Bluhm, M. Pierobon, J. Am. Chem. Soc. 1998, 120, 12849;
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 12849
-
-
Gansäuer, A.1
Bluhm, H.2
Pierobon, M.3
-
41
-
-
34547935055
-
-
g) L.-Z. Dai, M.-J. Qi, Y.-L. Shi, X.-G. Liu, M. Shi, Org. Lett. 2007, 9, 3191;
-
(2007)
Org. Lett
, vol.9
, pp. 3191
-
-
Dai, L.-Z.1
Qi, M.-J.2
Shi, Y.-L.3
Liu, X.-G.4
Shi, M.5
-
42
-
-
36749091693
-
-
h) X.-Z. Shu, X.-Y. Liu, H.-Q. Xiao, K.-G. Ji, L.-N. Guo, C.-Z. Qi, A.-M. Lian, Adv. Synth. Catal. 2007, 349, 2493;
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 2493
-
-
Shu, X.-Z.1
Liu, X.-Y.2
Xiao, H.-Q.3
Ji, K.-G.4
Guo, L.-N.5
Qi, C.-Z.6
Lian, A.-M.7
-
43
-
-
52049117956
-
-
i) M.-C. Cordonnier, A. Blanc, P. Pale, Org. Lett. 2008, 10, 1569;
-
(2008)
Org. Lett
, vol.10
, pp. 1569
-
-
Cordonnier, M.-C.1
Blanc, A.2
Pale, P.3
-
44
-
-
53849135573
-
-
j) A. S. K. Hashmi, M. Buhrle, R. Salathe, J. W. Bats, Adv. Synth. Catal. 2008, 350, 2059.
-
(2008)
Adv. Synth. Catal
, vol.350
, pp. 2059
-
-
Hashmi, A.S.K.1
Buhrle, M.2
Salathe, R.3
Bats, J.W.4
-
45
-
-
77149159537
-
-
Screening of catalyst activity for this transformation is provided in the Supporting Information
-
Screening of catalyst activity for this transformation is provided in the Supporting Information.
-
-
-
-
46
-
-
77149160688
-
-
1H NOE spectra of key compounds are provided in the Supporting Information.
-
1H NOE spectra of key compounds are provided in the Supporting Information.
-
-
-
-
47
-
-
34249056927
-
-
For metal-catalyzed intramolecular cycloaddition of allenes, see: a
-
For metal-catalyzed intramolecular cycloaddition of allenes, see: a) X. Huang, L. Zhang, J. Am. Chem. Soc. 2007, 129, 6398;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 6398
-
-
Huang, X.1
Zhang, L.2
-
48
-
-
35048851210
-
-
b) G. Zhang, V. J. Catalano, L. Zhang, J. Am. Chem. Soc. 2007, 129, 11358;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 11358
-
-
Zhang, G.1
Catalano, V.J.2
Zhang, L.3
-
50
-
-
54749116041
-
-
d) B. Trillo, F. López, M. Gulías, L. Castedo, J. L. Mascareñas, Angew. Chem. 2008, 120, 965;
-
(2008)
Angew. Chem
, vol.120
, pp. 965
-
-
Trillo, B.1
López, F.2
Gulías, M.3
Castedo, L.4
Mascareñas, J.L.5
-
54
-
-
63749113341
-
-
g) B. Trillo, F. López, S. Montserrat, G. Ujaque, L. Castedo, A. Lledós, J. L. MascareÇas, Chem. Eur. J. 2009, 15, 3336;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 3336
-
-
Trillo, B.1
López, F.2
Montserrat, S.3
Ujaque, G.4
Castedo, L.5
Lledós, A.6
MascareÇas, J.L.7
-
55
-
-
69949147971
-
-
h) P. Mauleón, R. M. Zeldin, A. Z. González, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6348;
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 6348
-
-
Mauleón, P.1
Zeldin, R.M.2
González, A.Z.3
Toste, F.D.4
-
56
-
-
67650292386
-
-
i) S. Yudha, Y. Kuninobu, K. Takai, Angew. Chem. 2008, 120, 9458;
-
(2008)
Angew. Chem
, vol.120
, pp. 9458
-
-
Yudha, S.1
Kuninobu, Y.2
Takai, K.3
-
58
-
-
69749114123
-
-
j) R. Chaudhuri, H.-Y. Liao, R.-S. Liu, Chem. Eur. J. 2009, 15, 8895;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 8895
-
-
Chaudhuri, R.1
Liao, H.-Y.2
Liu, R.-S.3
-
59
-
-
38049033193
-
-
k) H. Funami, H. Kusama, N. Iwasawa, Angew. Chem. 2007, 119, 927;
-
(2007)
Angew. Chem
, vol.119
, pp. 927
-
-
Funami, H.1
Kusama, H.2
Iwasawa, N.3
-
63
-
-
34250660123
-
-
m) G. Lemiére, V. Gandon, K. Cariou, T. Fukuyama, A.-L. Dhimane, L. Fensterbank, M. Malacria, Org. Lett. 2007, 9, 2207;
-
(2007)
Org. Lett
, vol.9
, pp. 2207
-
-
Lemiére, G.1
Gandon, V.2
Cariou, K.3
Fukuyama, T.4
Dhimane, A.-L.5
Fensterbank, L.6
Malacria, M.7
-
64
-
-
67749084445
-
-
n) G. Lemiére, V. Gandon, K. Cariou, A. Hours, T. Fukuyama, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2009, 131, 2993.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 2993
-
-
Lemiére, G.1
Gandon, V.2
Cariou, K.3
Hours, A.4
Fukuyama, T.5
Dhimane, A.-L.6
Fensterbank, L.7
Malacria, M.8
-
65
-
-
77149134090
-
-
When the strong nucleophile ROH replaced water in this catalysis, we observed diminished d.r. ratios of the resulting products 7a and 7e and their isomers 7a′ and 7e′. We note that the good d.r. value (d.r.> 20:1) was obtained for 7b/7b′ (R=Ph) because the cis-npentyl group of epoxide 1b impedes an external attack of the bulky phenol at the epoxy functionality. This side reaction is pronounced for small MeOH, giving 7a and 7a′ with a low d.r. value, Chemical Presented
-
When the strong nucleophile ROH replaced water in this catalysis, we observed diminished d.r. ratios of the resulting products 7a and 7e and their isomers 7a′ and 7e′. We note that the good d.r. value (d.r.> 20:1) was obtained for 7b/7b′ (R=Ph) because the cis-npentyl group of epoxide 1b impedes an external attack of the bulky phenol at the epoxy functionality. This side reaction is pronounced for small MeOH, giving 7a and 7a′ with a low d.r. value. (Chemical Presented)
-
-
-
-
66
-
-
77149125651
-
-
Preparation of chiral epoxide 4 is described in the Supporting Information.
-
Preparation of chiral epoxide 4 is described in the Supporting Information.
-
-
-
-
67
-
-
70450190983
-
-
Intermolecular [3+2] cycloaddition of an allene with an enol ether was reported with a platinum catalyst very recently, see H. Kusama, M. Ebisawa, H. Funami, N. Iwasawa, J. Am. Chem. Soc. 2009, 131, 16352.
-
Intermolecular [3+2] cycloaddition of an allene with an enol ether was reported with a platinum catalyst very recently, see H. Kusama, M. Ebisawa, H. Funami, N. Iwasawa, J. Am. Chem. Soc. 2009, 131, 16352.
-
-
-
-
68
-
-
77149172331
-
-
Catalyst screening for the cycloaddition of alcohol 2b with a diene is provided in the Supporting Information. The lower efficiency of the Brønsted acid is not surprising because cycloadducts 5a and 6a are sensitive to free protons.
-
Catalyst screening for the cycloaddition of alcohol 2b with a diene is provided in the Supporting Information. The lower efficiency of the Brønsted acid is not surprising because cycloadducts 5a and 6a are sensitive to free protons.
-
-
-
|