-
2
-
-
0036259981
-
-
K. C. Nicolaou, S. A. Snyder, T. Montagnon and G. Vassilikogiannakis, Angew. Chem., Int. Ed., 2002, 41, 1668.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 1668
-
-
Nicolaou, K.C.1
Snyder, S.A.2
Montagnon, T.3
Vassilikogiannakis, G.4
-
3
-
-
69949147971
-
-
P. Mauleón, R. M. Zeldin, A. Z. González and 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
-
4
-
-
70349159148
-
-
I. Alonso, B. Trillo, F. López, S. Montserrat, G. Ujaque, L. Castedo, A. Lledós and J. L. Mascareñas, J. Am. Chem. Soc., 2009, 131, 13020
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 13020
-
-
Alonso, I.1
Trillo, B.2
López, F.3
Montserrat, S.4
Ujaque, G.5
Castedo, L.6
Lledós, A.7
Mascareñas, J.L.8
-
5
-
-
70350676960
-
-
D. Benitez, E. Tkatchouk, A. Z. González, W. A. Goddard and F. D. Toste, Org. Lett., 2009, 11, 4798
-
(2009)
Org. Lett.
, vol.11
, pp. 4798
-
-
Benitez, D.1
Tkatchouk, E.2
González, A.Z.3
Goddard, W.A.4
Toste, F.D.5
-
7
-
-
77950224470
-
-
M. Alcarazo, T. Stork, A. Anoop, W. Thiel and A. Furstner, Angew. Chem., Int. Ed., 2010, 49, 2542.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 2542
-
-
Alcarazo, M.1
Stork, T.2
Anoop, A.3
Thiel, W.4
Furstner, A.5
-
8
-
-
0142213273
-
-
For a review on the synthetic utility of allenamides, see
-
For a review on the synthetic utility of allenamides, see: L.-L. Wei, H. Xiong and R. P. Hsung, Acc. Chem. Res., 2003, 36, 773.
-
(2003)
Acc. Chem. Res.
, vol.36
, pp. 773
-
-
Wei, L.-L.1
Xiong, H.2
Hsung, R.P.3
-
9
-
-
77955134646
-
-
For other types of Au-catalyzed reactions of allenamides, see
-
For other types of Au-catalyzed reactions of allenamides, see: A. W. Hill, M. R. J. Elsegood and M. C. Kimber, J. Org. Chem., 2010, 75, 5406
-
(2010)
J. Org. Chem.
, vol.75
, pp. 5406
-
-
Hill, A.W.1
Elsegood, M.R.J.2
Kimber, M.C.3
-
11
-
-
0031708442
-
-
For a Rh-catalyzed intermolecular cycloaddition between unactivated vinylallenes (4C) and alkynes (2C), see
-
For a Rh-catalyzed intermolecular cycloaddition between unactivated vinylallenes (4C) and alkynes (2C), see: M. Murakami, M. Ubukata, K. Itami and Y. Ito, Angew. Chem., Int. Ed., 1998, 37, 2248.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2248
-
-
Murakami, M.1
Ubukata, M.2
Itami, K.3
Ito, Y.4
-
12
-
-
70450190983
-
-
We are only aware of a Pt-catalyzed (3 + 2) cycloaddition of allenyl silyl ethers and enol ethers, see
-
We are only aware of a Pt-catalyzed (3 + 2) cycloaddition of allenyl silyl ethers and enol ethers, see: H. Kusama, M. Ebisawa, H. Funami and N. Iwasawa, J. Am. Chem. Soc., 2009, 131, 16352.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 16352
-
-
Kusama, H.1
Ebisawa, M.2
Funami, H.3
Iwasawa, N.4
-
13
-
-
70350496890
-
-
For recent reviews on Au-and Pt-catalyzed reactions, see
-
For recent reviews on Au-and Pt-catalyzed reactions, see: A. Fürstner, Chem. Soc. Rev., 2009, 38, 3208
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 3208
-
-
Fürstner, A.1
-
14
-
-
51049105959
-
-
D. J. Gorin, B. D. Sherry and F. D. Toste, Chem. Rev., 2008, 108, 3351
-
(2008)
Chem. Rev.
, vol.108
, pp. 3351
-
-
Gorin, D.J.1
Sherry, B.D.2
Toste, F.D.3
-
17
-
-
69949147971
-
-
Allenes and dienes may react in several ways in the presence of Au catalysts. For instance, we have shown that allenes can behave as 2C or 3C atom partners in their gold-catalyzed intramolecular cycloadditions with dienes, see, and
-
Allenes and dienes may react in several ways in the presence of Au catalysts. For instance, we have shown that allenes can behave as 2C or 3C atom partners in their gold-catalyzed intramolecular cycloadditions with dienes, see P. Mauleón, R. M. Zeldin, A. Z. González and F. D. Toste, J. Am. Chem. Soc., 2009, 131, 6348, and
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 6348
-
-
Mauleón, P.1
Zeldin, R.M.2
González, A.Z.3
Toste, F.D.4
-
18
-
-
38549092554
-
-
B. Trillo, F. López, M. Gulías, L. Castedo and J. L. Mascareñas, Angew. Chem., Int. Ed., 2008, 47, 951
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 951
-
-
Trillo, B.1
López, F.2
Gulías, M.3
Castedo, L.4
Mascareñas, J.L.5
-
19
-
-
63749113341
-
-
On the other hand, Au catalysts might also activate 1, 3-dienes
-
B. Trillo, F. López, S. Montserrat, G. Ujaque, L. Castedo, A. Lledós and J. L. Mascareñas, Chem.-Eur. J., 2009, 15, 3336. On the other hand, Au catalysts might also activate 1, 3-dienes
-
(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
Mascareñas, J.L.7
-
21
-
-
33745716289
-
-
C. Brouwer and C. He, Angew. Chem., Int. Ed., 2006, 45, 1744
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 1744
-
-
Brouwer, C.1
He, C.2
-
22
-
-
33745697752
-
-
R. V. Nguyen, X. Q. Yao and C. J. Li, Org. Lett., 2006, 8, 2397.
-
(2006)
Org. Lett.
, vol.8
, pp. 2397
-
-
Nguyen, R.V.1
Yao, X.Q.2
Li, C.J.3
-
23
-
-
79955581371
-
-
note
-
See the Supplementary Information† for more details.
-
-
-
-
24
-
-
0033578602
-
-
It has been shown that allenamides can participate in uncatalyzed hetero-(4 + 2) inverse electron demand Diels-Alder cycloadditions, see
-
It has been shown that allenamides can participate in uncatalyzed hetero-(4 + 2) inverse electron demand Diels-Alder cycloadditions, see: L.-L. Wei, H. Xiong, C. J. Douglas and R. P. Hsung, Tetrahedron Lett., 1999, 40, 6903
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 6903
-
-
Wei, L.-L.1
Xiong, H.2
Douglas, C.J.3
Hsung, R.P.4
-
25
-
-
0001703383
-
-
L.-L. Wei, R. P. Hsung, H. Xiong, J. A. Mulder and N. T. Nkansah, Org. Lett., 1999, 1, 2145
-
(1999)
Org. Lett.
, vol.1
, pp. 2145
-
-
Wei, L.-L.1
Hsung, R.P.2
Xiong, H.3
Mulder, J.A.4
Nkansah, N.T.5
-
27
-
-
0030995589
-
-
M. Kimura, Y. Wakamiya, Y. Horino and Y. Tamaru, Tetrahedron Lett., 1997, 38, 3963
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3963
-
-
Kimura, M.1
Wakamiya, Y.2
Horino, Y.3
Tamaru, Y.4
-
28
-
-
0038000454
-
-
Y. Horino, M. Kimura, S. Tanak, T. Okajima and Y. Tamaru, Chem.-Eur. J., 2003, 9, 2419.
-
(2003)
Chem.-Eur. J.
, vol.9
, pp. 2419
-
-
Horino, Y.1
Kimura, M.2
Tanak, S.3
Okajima, T.4
Tamaru, Y.5
-
29
-
-
0038616368
-
-
Two specific examples of normal electron demand (4 + 2) reactions have also been reported, see
-
Two specific examples of normal electron demand (4 + 2) reactions have also been reported, see: J. P. Bacci, K. L. Greenman and D. L. Van Vranken, J. Org. Chem., 2003, 68, 4955
-
(2003)
J. Org. Chem.
, vol.68
, pp. 4955
-
-
Bacci, J.P.1
Greenman, K.L.2
van Vranken, D.L.3
-
31
-
-
0030726933
-
-
For other types of (2 + 2) cycloadditions employing different allenamides, see
-
For other types of (2 + 2) cycloadditions employing different allenamides, see: M. Kimura, Y. Horino, Y. Wakamiya, T. Okayima and Y. Tamaru, J. Am. Chem. Soc., 1997, 119, 10869.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10869
-
-
Kimura, M.1
Horino, Y.2
Wakamiya, Y.3
Okayima, T.4
Tamaru, Y.5
-
32
-
-
77950224470
-
-
For Au-catalyzed intramolecular (2 + 2) cycloadditions of allenetethered alkenes, see
-
For Au-catalyzed intramolecular (2 + 2) cycloadditions of allenetethered alkenes, see M. Alcarazo, T. Stork, A. Anoop, W. Thiel and A. Furstner, Angew. Chem., Int. Ed., 2010, 49, 2542.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 2542
-
-
Alcarazo, M.1
Stork, T.2
Anoop, A.3
Thiel, W.4
Furstner, A.5
-
33
-
-
35349012652
-
-
and
-
and: M. R. Luzung, P. Mauleón and F. D. Toste, 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
-
34
-
-
77949418593
-
-
H. Teller, S. Flugge, R. Goddard and A. Fürstner, Angew. Chem., Int. Ed., 2010, 49, 1949.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 1949
-
-
Teller, H.1
Flugge, S.2
Goddard, R.3
Fürstner, A.4
-
35
-
-
75749141777
-
-
For a recent review on (2 + 2) cycloadditions of allenes, see
-
For a recent review on (2 + 2) cycloadditions of allenes, see: B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Soc. Rev., 2010, 39, 783.
-
(2010)
Chem. Soc. Rev.
, vol.39
, pp. 783
-
-
Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
-
36
-
-
77955799104
-
-
For a recent Au-catalyzed intermolecular (2 + 2) cycloaddition between alkynes and alkenes, see
-
For a recent Au-catalyzed intermolecular (2 + 2) cycloaddition between alkynes and alkenes, see: V. López-Carrillo and A. M. Echavarren, J. Am. Chem. Soc., 2010, 132, 9292-9294.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 9292-9294
-
-
López-Carrillo, V.1
Echavarren, A.M.2
-
37
-
-
79955604707
-
-
note
-
Additionally, in this reaction we also isolated a minor amount (17%) of the corresponding (2 + 2) adduct 4de.
-
-
-
-
38
-
-
79955603229
-
-
note
-
Submitting the (4 + 2) adduct 3dh to the reaction conditions provides 5dh, which confirms that 5dh is formed in situ from 3dh.
-
-
-
-
39
-
-
79955636020
-
-
note
-
Identification of isomeric adducts 3gi and 3gi' could be performed by NMR analysis. Moreover, the major isomer, 3gi, could be purified by crystallography, and further identified by X-ray diffraction
-
-
-
-
40
-
-
79955586719
-
-
note
-
The (2 + 2) adduct (4gi) was not detected.
-
-
-
-
41
-
-
67650333072
-
-
For different reactions on related enamides, see
-
For different reactions on related enamides, see: Diels-Alder, F. Gallier, H. Hussain, A. Martel, A. Kirschning and G. Dujardin, Org. Lett., 2009, 11, 3060
-
(2009)
Org. Lett.
, vol.11
, pp. 3060
-
-
Diels-Alder1
Gallier, F.2
Hussain, H.3
Martel, A.4
Kirschning, A.5
Dujardin, G.6
-
42
-
-
0042662014
-
-
Epoxidation
-
Epoxidation: W. Adam, S. G. Bosio, N. J. Turro and B. T. Wolff, Org. Lett., 2003, 5, 819
-
(2003)
Org. Lett.
, vol.5
, pp. 819
-
-
Adam, W.1
Bosio, S.G.2
Turro, N.J.3
Wolff, B.T.4
-
43
-
-
1442275451
-
-
W. Adam, S. G. Bosio and B. T. Wolff, J. Org. Chem., 2004, 69, 1704
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1704
-
-
Adam, W.1
Bosio, S.G.2
Wolff, B.T.3
-
44
-
-
0037205926
-
-
Photooxygenation
-
Photooxygenation: W. Adam, S. G. Bosio and N. J. Turro, J. Am. Chem. Soc., 2002, 124, 8814
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 8814
-
-
Adam, W.1
Bosio, S.G.2
Turro, N.J.3
-
45
-
-
35948948629
-
-
Halogenation
-
Halogenation: C. Ko, R. P. Hsung, Z. F. Al-Rashid, J. B. Feltenberger, T. Lu, H. J-Yang, Y. Wei and C. A. Zificsak, Org. Lett., 2007, 9, 4459
-
(2007)
Org. Lett.
, vol.9
, pp. 4459
-
-
Ko, C.1
Hsung, R.P.2
Al-Rashid, Z.F.3
Feltenberger, J.B.4
Lu, T.5
J-Yang, H.6
Wei, Y.7
Zificsak, C.A.8
-
46
-
-
77953013396
-
-
Hydrogenation
-
Hydrogenation: B. Gourdet, M. E. Rudkin and H. W. Lam, Org. Lett., 2010, 12, 2554
-
(2010)
Org. Lett.
, vol.12
, pp. 2554
-
-
Gourdet, B.1
Rudkin, M.E.2
Lam, H.W.3
-
47
-
-
78149436919
-
-
Asymmetric dihydroxylation
-
Asymmetric dihydroxylation: B. Gourdet and H. W. Lam, Angew. Chem., Int. Ed., 2010, 49, 8733.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 8733
-
-
Gourdet, B.1
Lam, H.W.2
|