-
1
-
-
70350496890
-
-
For recent reviews on gold catalysis, see
-
For recent reviews on gold catalysis, see: Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 3208
-
-
Fürstner, A.1
-
2
-
-
46649098072
-
-
Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4268
-
-
Michelet, V.1
Toullec, P.Y.2
Genêt, J.P.3
-
4
-
-
51049121927
-
-
Li, Z.; Brower, C.; He, C. Chem. Rev. 2008, 108, 3239
-
(2008)
Chem. Rev.
, vol.108
, pp. 3239
-
-
Li, Z.1
Brower, C.2
He, C.3
-
8
-
-
34250824768
-
-
Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 3410
-
-
Fürstner, A.1
Davies, P.W.2
-
9
-
-
48149105517
-
-
For selected examples of gold-catalyzed hydrofunctionalization of allenes, see
-
For selected examples of gold-catalyzed hydrofunctionalization of allenes, see: Lavallo, V.; Frey, G.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 5224
-
-
Lavallo, V.1
Frey, G.2
Donnadieu, B.3
Soleilhavoup, M.4
Bertrand, G.5
-
10
-
-
36448986032
-
-
Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 14148
-
-
Zhang, Z.1
Bender, C.F.2
Widenhoefer, R.A.3
-
11
-
-
33846047998
-
-
Zhang, Z.; Widenhoefer, R. Angew. Chem., Int. Ed. 2007, 46, 283
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 283
-
-
Zhang, Z.1
Widenhoefer, R.2
-
12
-
-
33847664670
-
-
LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 2452
-
-
Lalonde, R.L.1
Sherry, B.D.2
Kang, E.J.3
Toste, F.D.4
-
13
-
-
34548606671
-
-
Tarselli, M.; Chianese, A.; Lee, S.; Gagné, M. Angew. Chem., Int. Ed. 2007, 46, 6670
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 6670
-
-
Tarselli, M.1
Chianese, A.2
Lee, S.3
Gagné, M.4
-
14
-
-
33746048429
-
-
Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 9066
-
-
Zhang, Z.1
Liu, C.2
Kinder, R.E.3
Han, X.4
Qian, H.5
Widenhoefer, R.A.6
-
16
-
-
33744546269
-
-
Nishina, N.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3314
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 3314
-
-
Nishina, N.1
Yamamoto, Y.2
-
17
-
-
33646459632
-
-
Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957
-
(2006)
Org. Lett.
, vol.8
, pp. 1957
-
-
Buzas, A.1
Istrate, F.2
Gagosz, F.3
-
18
-
-
77952863831
-
-
Bolte, B.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 7294
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 7294
-
-
Bolte, B.1
Odabachian, Y.2
Gagosz, F.3
-
19
-
-
77949395209
-
-
Odabachian, Y.; Dias-Jurberg, I.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 3543
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3543
-
-
Odabachian, Y.1
Dias-Jurberg, I.2
Gagosz, F.3
-
20
-
-
75649110408
-
-
No example of a direct gold-catalyzed hydride transfer onto an allene has been reported. For examples of 1,5-hydride shifts observed in gold(I)-catalyzed processes, see
-
No example of a direct gold-catalyzed hydride transfer onto an allene has been reported. For examples of 1,5-hydride shifts observed in gold(I)-catalyzed processes, see: Harrak, Y.; Simonneau, A.; Malacria, M.; Gandon, V.; Fensterbank, L. Chem. Commun. 2010, 46, 865
-
(2010)
Chem. Commun.
, vol.46
, pp. 865
-
-
Harrak, Y.1
Simonneau, A.2
Malacria, M.3
Gandon, V.4
Fensterbank, L.5
-
21
-
-
70349934598
-
-
Jiménez-Núñez, E.; Raducan, M.; Lautenbach, T.; Molawi, K.; Solorio, C. R.; Echavarren, A. M. Angew. Chem., Int. Ed. 2009, 48, 6152
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6152
-
-
Jiménez-Núñez, E.1
Raducan, M.2
Lautenbach, T.3
Molawi, K.4
Solorio, C.R.5
Echavarren, A.M.6
-
22
-
-
67650551471
-
-
Cui, Li; Peng, Y.; Zhang, L. J. Am. Chem. Soc. 2009, 131, 8394
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 8394
-
-
Cui, L.1
Peng, Y.2
Zhang, L.3
-
25
-
-
67650311554
-
-
For examples of Lewis acid catalyzed sequences of a hydride transfer from an ether to an activated alkene followed by a cyclization, see
-
For examples of Lewis acid catalyzed sequences of a hydride transfer from an ether to an activated alkene followed by a cyclization, see: McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972
-
(2009)
Org. Lett.
, vol.11
, pp. 2972
-
-
McQuaid, K.M.1
Long, J.Z.2
Sames, D.3
-
28
-
-
53049091331
-
-
For the synthesis of gold complexes 12 and 13
-
For the synthesis of gold complexes 12 and 13, see: Amijs, C. H. M.; López-Carrillo; Raducan, V. M.; Pérez-Galán, P.; Ferrer, C.; Echavarren, A. M. J. Org. Chem. 2008, 73, 7721
-
(2008)
J. Org. Chem.
, vol.73
, pp. 7721
-
-
Amijs, C.H.M.1
López-Carrillo2
Raducan, V.M.3
Pérez-Galán, P.4
Ferrer, C.5
Echavarren, A.M.6
-
29
-
-
79957744254
-
-
1H NMR spectroscopy
-
1H NMR spectroscopy.
-
-
-
-
30
-
-
79957692107
-
-
The spiroether structural unit is found in a number of natural products
-
The spiroether structural unit is found in a number of natural products.
-
-
-
-
31
-
-
79957749459
-
-
The reaction could not be performed with monosubstituted allenes
-
The reaction could not be performed with monosubstituted allenes.
-
-
-
-
32
-
-
79957746255
-
-
(3) and the pendant alkene group in the chairlike transition state leading to intermediate 20 (see Scheme 1)
-
(3) and the pendant alkene group in the chairlike transition state leading to intermediate 20 (see Scheme 1).
-
-
-
-
33
-
-
79957693981
-
-
Compound 16e corresponds to an open form of the bicyclic compound generally obtained. Its formation probably results from a gold-catalyzed oxepane ring opening
-
Compound 16e corresponds to an open form of the bicyclic compound generally obtained. Its formation probably results from a gold-catalyzed oxepane ring opening.
-
-
-
-
34
-
-
35349012652
-
-
Luzung, M. R.; Mauleón, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12402
-
-
Luzung, M.R.1
Mauleón, P.2
Toste, F.D.3
-
36
-
-
79957715624
-
-
1H NMR spectroscopy
-
1H NMR spectroscopy.
-
-
-
-
37
-
-
79957744431
-
-
Compounds 10 and 11 remain unchanged when they were separately treated with gold catalyst 13 thus precluding the formation of 11 from 10 and 10 from 11
-
Compounds 10 and 11 remain unchanged when they were separately treated with gold catalyst 13 thus precluding the formation of 11 from 10 and 10 from 11.
-
-
-
-
38
-
-
79957703709
-
-
2 catalysis, and even after prolonged reaction times, compound 10 was not transformed into compound 11 thus precluding an isomerization of 10 into 18 via 20
-
2 catalysis, and even after prolonged reaction times, compound 10 was not transformed into compound 11 thus precluding an isomerization of 10 into 18 via 20.
-
-
-
-
39
-
-
79957763348
-
-
(3) in products 10(D) and 11(D) was equally shared between the two available positions. This specific pattern tends to show that no memory of chirality is involved in the hydroalkylation of allene 9. The nucleophilic trapping of oxonium 17 should proceed in this case with no facial selectivity
-
(3) in products 10(D) and 11(D) was equally shared between the two available positions. This specific pattern tends to show that no memory of chirality is involved in the hydroalkylation of allene 9. The nucleophilic trapping of oxonium 17 should proceed in this case with no facial selectivity.
-
-
-
-
40
-
-
0001397224
-
-
For a (3,5) oxonium-ene type cyclization leading to tetrahydropyrans of types 23 and 24, see
-
For a (3,5) oxonium-ene type cyclization leading to tetrahydropyrans of types 23 and 24, see: Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669
-
(2001)
Org. Lett.
, vol.3
, pp. 2669
-
-
Loh, T.-P.1
Hu, Q.-Y.2
Tan, K.-T.3
Cheng, H.-S.4
-
41
-
-
79957669348
-
-
1H NMR spectroscopy of the crude reaction mixture.
-
1H NMR spectroscopy of the crude reaction mixture.
-
-
-
-
42
-
-
79957569118
-
-
For a recent review on gold-mediated C-H bond functionalization, see
-
For a recent review on gold-mediated C-H bond functionalization, see: Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910
-
(2011)
Chem. Soc. Rev.
, vol.40
, pp. 1910
-
-
Boorman, T.C.1
Larrosa, I.2
|