-
1
-
-
0026418434
-
-
a) B. M. Trost, Science 1991, 254, 1471-1477:
-
(1991)
Science
, vol.254
, pp. 1471-1477
-
-
Trost, B.M.1
-
2
-
-
0027999819
-
-
b) N. Hall, Science 1994, 266, 32-34;
-
(1994)
Science
, vol.266
, pp. 32-34
-
-
Hall, N.1
-
3
-
-
0000791854
-
-
c) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
-
(1995)
Angew. Chem
, vol.107
, pp. 285-307
-
-
Trost, B.M.1
-
6
-
-
11244341464
-
-
Eds, F. Vögtle, J. F. Stoddart, M. Shibasaki, Wiley-VCH, Weinheim
-
a) L. F. Tietze, F. Hautner, in Stimulating Concepts in Chemistry (Eds.: F. Vögtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, p. 38;
-
(2000)
Stimulating Concepts in Chemistry
, pp. 38
-
-
Tietze, L.F.1
Hautner, F.2
-
7
-
-
0242613189
-
-
Ed, N. Hall, Cambridge University Press, Cambridge
-
b) K. C; Nicolaou, E. W. Yue, T. Oshima, in The New Chemistry (Ed.: N. Hall), Cambridge University Press, Cambridge. 2001, p. 168;
-
(2001)
The New Chemistry
, pp. 168
-
-
Nicolaou, K.C.1
Yue, E.W.2
Oshima, T.3
-
8
-
-
7044235263
-
-
c) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
-
(1996)
Chem. Rev
, vol.96
, pp. 115-136
-
-
Tietze, L.F.1
-
11
-
-
14244263496
-
-
For recent reviews on gold catalysis, see: a
-
For recent reviews on gold catalysis, see: a) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005. 3, 387-391;
-
(2005)
Org. Biomol. Chem
, vol.3
, pp. 387-391
-
-
Hoffmann-Röder, A.1
Krause, N.2
-
13
-
-
13744249187
-
-
Angew. Chem. Int. Ed. 2005, 44, 850-852;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 850-852
-
-
-
15
-
-
27744595601
-
-
Angew. Chem. Int. Ed. 2005, 44, 6990-6993;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 6990-6993
-
-
-
17
-
-
33845546747
-
-
Angew. Chem. Int. Ed. 2006, 45, 7896-7936:
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 7896-7936
-
-
-
19
-
-
34547510627
-
-
f) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211:
-
(2007)
Chem. Rev
, vol.107
, pp. 3180-3211
-
-
Hashmi, A.S.K.1
-
21
-
-
34250824768
-
-
Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 3410-3449
-
-
-
23
-
-
4544255270
-
-
For select examples of gold-catalyzed tandem C-C and C-X bond formations, see: a T. Yao, X. Zhang, R. C.; Larock, J. Am. Chem. Soc 2004, 126, 11164-11165:
-
For select examples of gold-catalyzed tandem C-C and C-X bond formations, see: a) T. Yao, X. Zhang, R. C.; Larock, J. Am. Chem. Soc 2004, 126, 11164-11165:
-
-
-
-
24
-
-
22144454984
-
-
b) J.R Markham, S.T. Staben, F.D. Toste, J. Am. Chem. Soc 2005, 127, 9708-9709;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 9708-9709
-
-
Markham, J.R.1
Staben, S.T.2
Toste, F.D.3
-
26
-
-
33750080351
-
-
d) J. Barluenga, A. Diéguez, A. Fernández, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2006, 118, 2145-2147:
-
(2006)
Angew. Chem
, vol.118
, pp. 2145-2147
-
-
Barluenga, J.1
Diéguez, A.2
Fernández, A.3
Rodríguez, F.4
Fañanás, F.J.5
-
27
-
-
33745661090
-
-
Angew. Chem. Int. Ed. 2006, 45, 2091-2093;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 2091-2093
-
-
-
29
-
-
33750156253
-
-
Angew. Chem. Int. Ed. 2006, 45, 6704-6707;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 6704-6707
-
-
-
30
-
-
33745677660
-
-
f) B. D. Sherry, L. Maus, B. N. Laforteza, F.D. Toste, J. Am. Chem. Soc. 2006, 128, 8132-8133;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 8132-8133
-
-
Sherry, B.D.1
Maus, L.2
Laforteza, B.N.3
Toste, F.D.4
-
31
-
-
35048843671
-
-
g) T. Yang, L. Campbell, D. J. Dixon, J. Am. Chem. Soc. 2007, 129, 12070-12071;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 12070-12071
-
-
Yang, T.1
Campbell, L.2
Dixon, D.J.3
-
33
-
-
36048953800
-
-
Angew. Chem. Int. Ed. 2007, 46, 8250-8253.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 8250-8253
-
-
-
34
-
-
34250840234
-
-
a) I. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585-4587;
-
(2006)
Angew. Chem
, vol.118
, pp. 4585-4587
-
-
Nakamura, I.1
Sato, T.2
Yamamoto, Y.3
-
35
-
-
33746309818
-
-
Angew. Chem. Int. Ed., 2006, 45, 4473-4475;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 4473-4475
-
-
-
36
-
-
34250640281
-
-
b) S. F. Kirsch, J. T. Binder, .C Liébert, H. Menz, Angew. Chem. 2006, 118, 6010-6013:
-
(2006)
Angew. Chem
, vol.118
, pp. 6010-6013
-
-
Kirsch, S.F.1
Binder, J.T.2
Liébert, C.3
Menz, H.4
-
37
-
-
33748529350
-
-
Angew. Chem. Int. Ed. 2006, 45, 5878-5880;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 5878-5880
-
-
-
39
-
-
34447298790
-
-
d) S. F. Kirsch, J. T. Binder, B. Crone. A. Duschek, T. T. Haug, C. Liébert, H. Menz, Angew. Chem. 2007, 119, 2360-2363;
-
(2007)
Angew. Chem
, vol.119
, pp. 2360-2363
-
-
Kirsch, S.F.1
Binder, J.T.2
Crone, B.3
Duschek, A.4
Haug, T.T.5
Liébert, C.6
Menz, H.7
-
40
-
-
34250333483
-
-
Angew. Chem. Int. Ed. 2007, 46, 2310-2313;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 2310-2313
-
-
-
42
-
-
34447342869
-
-
Angew. Chem. Int. Ed. 2007, 46, 5195-5197.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 5195-5197
-
-
-
43
-
-
0000396789
-
-
For gold-catalyzed migration induced by carbonyl groups, see: a
-
For gold-catalyzed migration induced by carbonyl groups, see: a) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T.M. Frost, Angew. Chem. 2000, 112, 2382-2385;
-
(2000)
Angew. Chem
, vol.112
, pp. 2382-2385
-
-
Hashmi, A.S.K.1
Schwarz, L.2
Choi, J.-H.3
Frost, T.M.4
-
44
-
-
0034600902
-
-
Angew. Chem. Int. Ed. 2000, 39, 2285-2288:
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 2285-2288
-
-
-
45
-
-
23044485049
-
-
b) A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc 2005, 127, 10500-10501;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 10500-10501
-
-
Sromek, A.W.1
Rubina, M.2
Gevorgyan, V.3
-
46
-
-
53949110475
-
-
ref. [5b]; d) ref. [5e]; for other types of metal-catalyzed reactions, see: e J. T. Kim, A. V. KelGin, V. Gevorgyan, Angew. Chem. 2003, 115, 102-105;
-
c) ref. [5b]; d) ref. [5e]; for other types of metal-catalyzed reactions, see: e) J. T. Kim, A. V. KelGin, V. Gevorgyan, Angew. Chem. 2003, 115, 102-105;
-
-
-
-
47
-
-
53949107127
-
-
Angew. Chem. Int. Ed. 2003, 42, 98-101;
-
(2003)
Angew. Chem. Int. Ed
, vol.42
, pp. 98-101
-
-
-
48
-
-
13744250442
-
-
f) A. W. Sromek, A. V. KelGin, V. Gevorgyan, Angew. Chem. 2004, 116, 2330-2332;
-
(2004)
Angew. Chem
, vol.116
, pp. 2330-2332
-
-
Sromek, A.W.1
KelGin, A.V.2
Gevorgyan, V.3
-
49
-
-
4544333104
-
-
Angew. Chem. Int. Ed. 2004, 43, 2280-2282.
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 2280-2282
-
-
-
51
-
-
23744449320
-
-
a) X. H. Duan, X. Y. Liu, L. N. Guo, M. C. Liao, W. M. Liu, Y. M. Liang, J. Org. Chem. 2005, 70, 6980-6983;
-
(2005)
J. Org. Chem
, vol.70
, pp. 6980-6983
-
-
Duan, X.H.1
Liu, X.Y.2
Guo, L.N.3
Liao, M.C.4
Liu, W.M.5
Liang, Y.M.6
-
52
-
-
33747048684
-
-
b) X. Liu, Z. Pan, X. Shu, X. Duan, Y. Liang, Synlett 2006, 1962-1964;
-
(2006)
Synlett
, pp. 1962-1964
-
-
Liu, X.1
Pan, Z.2
Shu, X.3
Duan, X.4
Liang, Y.5
-
53
-
-
53949114601
-
-
c) H. P. Bi, X. Y. Liu, F. R. Gou, L. N. Guo, X. H. Duan, X. Z. Shu, Y. M. Liang, Angew. Chem. 2007, 119, 7198-7201;
-
(2007)
Angew. Chem
, vol.119
, pp. 7198-7201
-
-
Bi, H.P.1
Liu, X.Y.2
Gou, F.R.3
Guo, L.N.4
Duan, X.H.5
Shu, X.Z.6
Liang, Y.M.7
-
54
-
-
34848888306
-
-
Angew. Chem. Int. Ed. 2007, 46. 7068-7071;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 7068-7071
-
-
-
55
-
-
36749091693
-
-
d) X. Z. Shu, X. Y. Liu, H. Q. Xiao, K. G. Ji, L. N. Guo, C. Z. Qi, Y. M. Liang, Adv. Synth. Catal. 2007, 349, 2493-2498;
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 2493-2498
-
-
Shu, X.Z.1
Liu, X.Y.2
Xiao, H.Q.3
Ji, K.G.4
Guo, L.N.5
Qi, C.Z.6
Liang, Y.M.7
-
56
-
-
38849143246
-
-
e) X. Z. Shu, X. Y. Liu, H. Q. Xiao, K. G. Ji, L. N. Guo, Y. M. Liang. Adv. Synth. Catal. 2008, 350, 243-248.
-
(2008)
Adv. Synth. Catal
, vol.350
, pp. 243-248
-
-
Shu, X.Z.1
Liu, X.Y.2
Xiao, H.Q.3
Ji, K.G.4
Guo, L.N.5
Liang, Y.M.6
-
57
-
-
53949100585
-
-
For some examples of this strategy, see: a
-
For some examples of this strategy, see: a) Ref. [8d];
-
, vol.8 d
-
-
Ref1
-
61
-
-
33744801116
-
-
e) B. G. Pujanauski, B. A. Bhanu Prasad, R. Sarpong, J. Am. Chem. Soc. 2006, 128, 6786-6787.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 6786-6787
-
-
Pujanauski, B.G.1
Bhanu Prasad, B.A.2
Sarpong, R.3
-
62
-
-
53949100804
-
-
See the Supporting Information for details
-
See the Supporting Information for details.
-
-
-
-
63
-
-
53949104664
-
-
The result was improved efficiently by switching the solvent to benzene: however, the toxicity of the benzene should be noted
-
The result was improved efficiently by switching the solvent to benzene: however, the toxicity of the benzene should be noted.
-
-
-
-
64
-
-
53949105179
-
-
The molecular structure of the corresponding product Im was determined by means of X-ray crystallographic studies; for details, see the Supporting Information, CCDC 668682 (1m) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
The molecular structure of the corresponding product Im was determined by means of X-ray crystallographic studies; for details, see the Supporting Information : CCDC 668682 (1m) 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.
-
-
-
-
65
-
-
53949101014
-
-
1H NMR NOE interaction studies.
-
1H NMR NOE interaction studies.
-
-
-
-
66
-
-
53949094282
-
-
II; see: ref. [9b].
-
II; see: ref. [9b].
-
-
-
-
67
-
-
0025788674
-
-
For a full explanation and definition of the terms syn and anti as used herein, see: C.M. Marson, D. W. M. Benzies, A.D. Hobson, Tetrahedron 1991, 47, 5491-5506.
-
For a full explanation and definition of the terms syn and anti as used herein, see: C.M. Marson, D. W. M. Benzies, A.D. Hobson, Tetrahedron 1991, 47, 5491-5506.
-
-
-
-
68
-
-
0001647186
-
-
For select examples of a Lewis acid promoted semipinacol rear-rangement of α-hydroxy epoxides, see: a
-
For select examples of a Lewis acid promoted semipinacol rear-rangement of α-hydroxy epoxides, see: a) Y. Q. Tu, L. D. Sun, P. Z. Wang, J. Org. Chem. 1999, 64, 629-633;
-
(1999)
J. Org. Chem
, vol.64
, pp. 629-633
-
-
Tu, Y.Q.1
Sun, L.D.2
Wang, P.Z.3
-
69
-
-
0141430597
-
-
b) C. A. Fan, B. M. Wang, Y. Q. Tu, Z. L. Song, Angew. Chem. 2001, 113, 3995-3998:
-
(2001)
Angew. Chem
, vol.113
, pp. 3995-3998
-
-
Fan, C.A.1
Wang, B.M.2
Tu, Y.Q.3
Song, Z.L.4
-
70
-
-
0035887126
-
-
Angew. Chem. Int. Ed. 2001, 40, 3877-3880;
-
(2001)
Angew. Chem. Int. Ed
, vol.40
, pp. 3877-3880
-
-
-
71
-
-
12444301519
-
-
c) X. D. Hu, C. A. Fan, F. M. Zhang, Y. Q. Tu, Angew. Chem. 2004, 116, 1734-1737:
-
(2004)
Angew. Chem
, vol.116
, pp. 1734-1737
-
-
Hu, X.D.1
Fan, C.A.2
Zhang, F.M.3
Tu, Y.Q.4
-
72
-
-
4043081489
-
-
Angew. Chem. Int. Ed. 2004, 43, 1702-1705.
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 1702-1705
-
-
-
73
-
-
53949121519
-
-
The mechanism for the formation of 4d is likely to be
-
The mechanism for the formation of 4d is likely to be.
-
-
-
-
74
-
-
53949109999
-
-
Although we could not exclude the semipinacol rearrangement from the mechanism, we still insist that the oxonium ion is an the intermediate in the process. The results of acyclic systems are most consistem with our hypothesis (Table 3, entries 1-3, and the high stereoselectivity of the transformation is also consistent with this hypothesis; furthermore, we studied the semipinacol rearrangement of 3d and no semipinacol rearrangement product was detected Table 3. entry 4, We also did not observe any semipinacol rear-rangement product I, which might have been detected in the reaction. For an alternate mechanism by semipinacol rearrangement, see
-
Although we could not exclude the semipinacol rearrangement from the mechanism, we still insist that the oxonium ion is an the intermediate in the process. The results of acyclic systems are most consistem with our hypothesis (Table 3, entries 1-3), and the high stereoselectivity of the transformation is also consistent with this hypothesis; furthermore, we studied the semipinacol rearrangement of 3d and no semipinacol rearrangement product was detected (Table 3. entry 4). We also did not observe any semipinacol rear-rangement product I, which might have been detected in the reaction. For an alternate mechanism by semipinacol rearrangement, see:
-
-
-
-
75
-
-
2942682670
-
-
Some reactions concerning the oxonium ion. see: a
-
Some reactions concerning the oxonium ion. see: a) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458-7459;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 7458-7459
-
-
Asao, N.1
Aikawa, H.2
Yamamoto, Y.3
-
76
-
-
4344709811
-
-
b) J. Zhu, A. R. Germain, J.A.J. Porco, Angew. Chem. 2004, 116, 1259-1263:
-
(2004)
Angew. Chem
, vol.116
, pp. 1259-1263
-
-
Zhu, J.1
Germain, A.R.2
Porco, J.A.J.3
-
77
-
-
2942631590
-
-
Angew. Chem. Int. Ed. 2004, 43, 1239-1243:
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 1239-1243
-
-
-
78
-
-
14744267835
-
-
c) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709-2716;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2709-2716
-
-
Kusama, H.1
Funami, H.2
Shido, M.3
Hara, Y.4
Takaya, J.5
Iwasawa, N.6
-
79
-
-
53949108489
-
-
refs [6, 9
-
d) refs [6, 9].
-
-
-
-
80
-
-
0028133271
-
-
J. R. Dimmock, K. K. Sidhu, M. Chen, J. Li, J. W. Quail, T. M. Allen, G. Y. Kao, J. Pharm. Sci. 1994, 83, 852-858.
-
(1994)
J. Pharm. Sci
, vol.83
, pp. 852-858
-
-
Dimmock, J.R.1
Sidhu, K.K.2
Chen, M.3
Li, J.4
Quail, J.W.5
Allen, T.M.6
Kao, G.Y.7
-
82
-
-
0000779895
-
-
S. V. Kelkar, A. A. Arbale, G. S. Joshi, G. H. Kulkarni, Synth. Commun. 1990, 20, 839-847.
-
(1990)
Synth. Commun
, vol.20
, pp. 839-847
-
-
Kelkar, S.V.1
Arbale, A.A.2
Joshi, G.S.3
Kulkarni, G.H.4
|