-
1
-
-
17844386379
-
-
Bermejo, A.; Figadère, B.; Zafra-Polo, M.-C.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269-303.
-
(2005)
Nat. Prod. Rep.
, vol.22
, pp. 269-303
-
-
Bermejo, A.1
Figadère, B.2
Zafra-Polo, M.-C.3
Barrachina, I.4
Estornell, E.5
Cortes, D.6
-
2
-
-
2442452788
-
-
(a) Han, H.; Sinha, M. K.; D'Souza, L. J.; Keinan, E.; Sinha, S. C. Chem-Eur. J. 2004, 10, 2149-2158.
-
(2004)
Chem-Eur. J.
, vol.10
, pp. 2149-2158
-
-
Han, H.1
Sinha, M.K.2
D'Souza, L.J.3
Keinan, E.4
Sinha, S.C.5
-
3
-
-
20444448544
-
-
(b) Derbré, S.; Roué, G.; Poupon, E.; Susin, S. A.; Hocquemiller, R. ChemBioChem 2005, 6, 979-982.
-
(2005)
ChemBioChem
, vol.6
, pp. 979-982
-
-
Derbré, S.1
Roué, G.2
Poupon, E.3
Susin, S.A.4
Hocquemiller, R.5
-
5
-
-
0017850469
-
-
(a) Fukuyama, T.; Vranesic, B.; Negri, D. P.; Kishi, Y. Tetrahedron Lett. 1978, 19, 2741-2744.
-
(1978)
Tetrahedron Lett.
, vol.19
, pp. 2741-2744
-
-
Fukuyama, T.1
Vranesic, B.2
Negri, D.P.3
Kishi, Y.4
-
8
-
-
65249167127
-
-
Kang, B.; Mowat, J.; Pinter, T.; Britton, R. Org. Lett. 2009, 11, 1717-1720.
-
(2009)
Org. Lett.
, vol.11
, pp. 1717-1720
-
-
Kang, B.1
Mowat, J.2
Pinter, T.3
Britton, R.4
-
10
-
-
11144273879
-
-
(b) Caserta, T.; Piccialli, V.; Gomez-Paloma, L.; Bifulco, G. Tetrahedron 2005, 61, 927-939.
-
(2005)
Tetrahedron
, vol.61
, pp. 927-939
-
-
Caserta, T.1
Piccialli, V.2
Gomez-Paloma, L.3
Bifulco, G.4
-
13
-
-
0034719252
-
-
(b) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223-226.
-
(2000)
Org. Lett.
, vol.2
, pp. 223-226
-
-
Hanaki, N.1
Link, J.T.2
MacMillan, D.W.C.3
Overman, L.E.4
Trankle, W.G.5
Wurster, J.A.6
-
14
-
-
0031843545
-
-
(a) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 4876-4877.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4876-4877
-
-
Schaus, S.E.1
Branalt, J.2
Jacobsen, E.N.3
-
15
-
-
0030971552
-
-
(b) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 257-259
-
-
Schneider, M.F.1
Lucas, N.2
Velder, J.3
Blechert, S.4
-
16
-
-
0035861034
-
-
Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 11312-11313
-
-
Louie, J.1
Bielawski, C.W.2
Grubbs, R.H.3
-
21
-
-
0000158579
-
-
(b) Lee, E.; Song, H. Y.; Kim, H. J. J. Chem. Soc., Perkin Trans. 1 1999, 3395-3396.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 3395-3396
-
-
Lee, E.1
Song, H.Y.2
Kim, H.J.3
-
23
-
-
49849095367
-
-
(a) Mitchell, T. A.; Zhao, C.; Romo, D. Angew. Chem., Int. Ed. 2008, 47, 5026-5029.
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 5026-5029
-
-
Mitchell, T.A.1
Zhao, C.2
Romo, D.3
-
25
-
-
0343778881
-
-
Selected examples
-
Review: (a) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 12931316. Selected examples:
-
(1995)
Chem. Rev.
, vol.95
, pp. 12931316
-
-
Masse, C.E.1
Panek, J.S.2
-
27
-
-
25444504067
-
-
Mertz, E.; Tinsley, J. M.; Roush, W. R. J. Org. Chem. 2005, 70, 8035-8046.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 8035-8046
-
-
Mertz, E.1
Tinsley, J.M.2
Roush, W.R.3
-
28
-
-
0042468148
-
-
Gansäuer, A.; Rinker, B.; Pierobon, M.; Grimme, S.; Gerenkamp, M.; Mück-Lichtenfeld, C. Angew. Chem., Int. Ed. 2003, 42, 3687-3690.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3687-3690
-
-
Gansäuer, A.1
Rinker, B.2
Pierobon, M.3
Grimme, S.4
Gerenkamp, M.5
Mück-Lichtenfeld, C.6
-
30
-
-
0026714006
-
-
(b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599. For selected examples, see:
-
(1992)
Tetrahedron
, vol.48
, pp. 8545-8599
-
-
Postema, M.H.D.1
-
36
-
-
23744510729
-
-
(b) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879-10884.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 10879-10884
-
-
Larsen, C.H.1
Ridgway, B.H.2
Shaw, J.T.3
Smith, D.M.4
Woerpel, K.A.5
-
37
-
-
69449102375
-
-
See page 10881 of ref 14b
-
See page 10881 of ref 14b.
-
-
-
-
38
-
-
69449105738
-
-
See page 3894 of ref 13
-
See page 3894 of ref 13.
-
-
-
-
39
-
-
42249089076
-
-
For a review, see ref 3. Selected recent examples: (a)
-
For a review, see ref 3. Selected recent examples: (a) Donohoe, T. J.; Williams, O.; Churchill, G. H. Angew. Chem, Int. Ed. 2008, 47, 28692871.
-
(2008)
Angew. Chem, Int. Ed.
, vol.47
, pp. 28692871
-
-
Donohoe, T.J.1
Williams, O.2
Churchill, G.H.3
-
41
-
-
52149116062
-
-
Menendez Perez, B.; Schuch, D.; Hartung, J. Org. Biomol. Chem. 2008, 6, 3532-3541.
-
(2008)
Org. Biomol. Chem.
, vol.6
, pp. 3532-3541
-
-
Menendez Perez, B.1
Schuch, D.2
Hartung, J.3
-
42
-
-
58149293591
-
-
Fernandez de la Pradilla, R.; Castellanos, A.; Osante, I.; Colomer, I.; Sanchez, M. I. J. Org. Chem. 2009, 74, 170-181.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 170-181
-
-
De La Fernandez Pradilla, R.1
Castellanos, A.2
Osante, I.3
Colomer, I.4
Sanchez, M.I.5
-
46
-
-
0033597981
-
-
(a) Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245-9260.
-
(1999)
Tetrahedron
, vol.55
, pp. 9245-9260
-
-
Jaouen, V.1
Jegou, A.2
Lemee, L.3
Veyrieres, A.4
-
47
-
-
0033757533
-
-
More substituted cases may be less selective
-
(b) More substituted cases may be less selective: Kovensky, J.; Sinay, P. Eur. J. Org. Chem. 2000, 3523-3525;
-
(2000)
Eur. J. Org. Chem.
, pp. 3523-3525
-
-
Kovensky, J.1
Sinay, P.2
-
48
-
-
69449101259
-
-
correction Eur. J. Org. Chem. 2000, 4125.
-
(2000)
Eur. J. Org. Chem.
, pp. 4125
-
-
-
49
-
-
28444473884
-
-
For relevant computational studies, see
-
For relevant computational studies, see: Nokami, T.; Werz, D. B.; Seeberger, P. H. Helv. Chim. Acta 2005, 88, 2823-2831.
-
(2005)
Helv. Chim. Acta
, vol.88
, pp. 2823-2831
-
-
Nokami, T.1
Werz, D.B.2
Seeberger, P.H.3
-
51
-
-
0017632053
-
-
(b) Hall, H. K., Jr.; DeBlauwe, F.; Carr, L. J.; Rao, V. S.; Reddy, G. S. J. Polym. Sci. Polym. Symp. 1976, 56, 101-115.
-
(1976)
J. Polym. Sci. Polym. Symp.
, vol.56
, pp. 101-115
-
-
Hall Jr.1
, H.K.2
Deblauwe, F.3
Carr, L.J.4
Rao, V.S.5
Reddy, G.S.6
-
52
-
-
69449086693
-
-
Enhanced reactivity of 1 suggests that the range of conditions suitable for initiation of its reactions (i.e., combinations of Lewis acids and nucleophiles) might be broader than for other types of acetals
-
Enhanced reactivity of 1 suggests that the range of conditions suitable for initiation of its reactions (i.e., combinations of Lewis acids and nucleophiles) might be broader than for other types of acetals.
-
-
-
-
53
-
-
0031457848
-
-
Bakina, E.; Wu, Z.; Rosenblum, M.; Farquhar, D. J. Med. Chem. 1997, 40, 4013-4018.
-
(1997)
J. Med. Chem.
, vol.40
, pp. 4013-4018
-
-
Bakina, E.1
Wu, Z.2
Rosenblum, M.3
Farquhar, D.4
-
54
-
-
69449089860
-
-
Diol 3 has also been prepared in enantiomerically enriched form
-
Diol 3 has also been prepared in enantiomerically enriched form. Raifeld, Y. E.; Nikitenko, A. A.; Arshava, B. M.; Mikerin, I. E.; Zilberg, L. L.; Vid, G. Y.; Lang, S. A., Jr.; Lee, V. J. Tetrahedron 1994, 50, 86038616.
-
(1994)
Tetrahedron
, vol.50
, pp. 86038616
-
-
Raifeld, Y.E.1
Nikitenko, A.A.2
Arshava, B.M.3
Mikerin, I.E.4
Zilberg, L.L.5
Vid, G.Y.6
Lang Jr.7
, S.A.8
Lee, V.J.9
-
55
-
-
69449105584
-
-
Hall reported a yield of 85% of 1 using lower pressure and mechanical stirring. See ref 20b
-
Hall reported a yield of 85% of 1 using lower pressure and mechanical stirring. See ref 20b.
-
-
-
-
56
-
-
0034703157
-
-
Compounds 4a, 4b, and 4e were identified by comparison to literature data, (a) 4a
-
Compounds 4a, 4b, and 4e were identified by comparison to literature data, (a) 4a: Pilli, R. A.; Riatto, V. B. Tetrahedron: Asymmetry 2000, 11, 3675-3686.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 3675-3686
-
-
Pilli, R.A.1
Riatto, V.B.2
-
57
-
-
33746087596
-
-
4b
-
(b) 4b: Freifeld, I.; Holtz, E.; Dahmann, G.; Langer, P. Eur. J. Org. Chem. 2006, 3251-3258.
-
(2006)
Eur. J. Org. Chem.
, pp. 3251-3258
-
-
Freifeld, I.1
Holtz, E.2
Dahmann, G.3
Langer, P.4
-
58
-
-
0027472613
-
-
Bunn, B. J.; Cox, P. J.; Simpkins, N. S. Tetrahedron 1993, 49, 207-218.
-
(1993)
Tetrahedron
, vol.49
, pp. 207-218
-
-
Bunn, B.J.1
Cox, P.J.2
Simpkins, N.S.3
-
59
-
-
0025726135
-
-
Iqbal, J.; Pandey, A.; Chauhan, B. P. S. Tetrahedron 1991, 47, 4143-4154.
-
(1991)
Tetrahedron
, vol.47
, pp. 4143-4154
-
-
Iqbal, J.1
Pandey, A.2
Chauhan, B.P.S.3
-
60
-
-
4444301839
-
-
4e
-
4e: Chakraborty, T. K.; Reddy, V. R.; Sudhakar, G.; Kumar, S. U.; Reddy, T. J.; Kumar, S. K.; Kunwar, A. C.; Mathur, A.; Sharma, R.; Gupta, N.; Prasad, S. Tetrahedron 2004, 60, 8329-8339.
-
(2004)
Tetrahedron
, vol.60
, pp. 8329-8339
-
-
Chakraborty, T.K.1
Reddy, V.R.2
Sudhakar, G.3
Kumar, S.U.4
Reddy, T.J.5
Kumar, S.K.6
Kunwar, A.C.7
Mathur, A.8
Sharma, R.9
Gupta, N.10
Prasad, S.11
-
61
-
-
0001151568
-
-
(a) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107-6115.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 6107-6115
-
-
Mori, I.1
Ishihara, K.2
Flippin, L.A.3
Nozaki, K.4
Yamamoto, H.5
Bartlett, P.A.6
Heathcock, C.H.7
-
64
-
-
58149154432
-
-
For discussions of the role of ion-pairing on stereocontrol in additions to cyclic oxocarbenium ions, see: (a)
-
For discussions of the role of ion-pairing on stereocontrol in additions to cyclic oxocarbenium ions, see: (a) Krumper, J. R.; Salamant, W. A.; Woerpel, K. A. Org. Lett. 2008, 10, 4907-4910.
-
(2008)
Org. Lett.
, vol.10
, pp. 4907-4910
-
-
Krumper, J.R.1
Salamant, W.A.2
Woerpel, K.A.3
-
66
-
-
0037151613
-
-
Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720-9721.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9720-9721
-
-
Zhang, Y.1
Reynolds, N.T.2
Manju, K.3
Rovis, T.4
-
67
-
-
0842307518
-
-
For related mechanistic features, see: (a) Also see
-
For related mechanistic features, see: (a) Braun, M.; Kotter, W. Angew Chem., Int. Ed. 2004, 43, 514-517. Also see:
-
(2004)
Angew Chem., Int. Ed.
, vol.43
, pp. 514-517
-
-
Braun, M.1
Kotter, W.2
-
68
-
-
44949230317
-
-
(b) Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198-7199.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 7198-7199
-
-
Reisman, S.E.1
Doyle, A.G.2
Jacobsen, E.N.3
-
69
-
-
0030973398
-
-
2 in the reaction of acyclic chiral acetais with allylsilane reagents, (a)
-
2 in the reaction of acyclic chiral acetais with allylsilane reagents, (a) Matsutani, H.; Ichikawa, S.; Yaruva, J.; Kusumoto, T.; Hiyama, T. J. Am. Chem. Soc. 1997, 119, 4541-4542.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4541-4542
-
-
Matsutani, H.1
Ichikawa, S.2
Yaruva, J.3
Kusumoto, T.4
Hiyama, T.5
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