-
1
-
-
20544450502
-
-
Wiley-VCH: Weinheim, Germany
-
(a) For examples of Pd(0)-catalyzed cross-coupling, see: Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
-
-
De Meijere, A.1
Diederich, F.2
-
2
-
-
0003535745
-
-
Miyaura, N., Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin
-
Cross-Coupling Reactions - A Practical Guide; Miyaura, N., Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin, 2002; Vol. 219.
-
(2002)
Cross-Coupling Reactions - A Practical Guide
, vol.219
-
-
-
5
-
-
0004246896
-
-
Krause, N., Ed.; Wiley-VCH: Weinheim, Germany
-
Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
-
(2002)
Modern Organocopper Chemistry
-
-
-
6
-
-
28744437502
-
-
O'Neil, I. A., Ed.; Thieme Verlag: Stuttgart, Germany
-
Heaney, H.; Christie, S. In Science of Synthesis; O'Neil, I. A., Ed.; Thieme Verlag: Stuttgart, Germany, 2004; Vol. 3, pp 305-662.
-
(2004)
Science of Synthesis
, vol.3
, pp. 305-662
-
-
Heaney, H.1
Christie, S.2
-
7
-
-
0004228992
-
-
Taylor, R. J. K., Ed.; IRL Press: Oxford
-
Organocopper Reagents; Taylor, R. J. K., Ed.; IRL Press: Oxford, 1994.
-
(1994)
Organocopper Reagents
-
-
-
9
-
-
0012689858
-
-
Takai, K.; Nozaki, H. Proc. Jpn. Acad., Ser. B 2000, 76, 123-131.
-
(2000)
Proc. Jpn. Acad., Ser. B
, vol.76
, pp. 123-131
-
-
Takai, K.1
Nozaki, H.2
-
11
-
-
0033460956
-
-
Avalos, M.; Babiano, R.; Cintas, P.; Jiminez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169-177.
-
(1999)
Chem. Soc. Rev.
, vol.28
, pp. 169-177
-
-
Avalos, M.1
Babiano, R.2
Cintas, P.3
Jiminez, J.L.4
Palacios, J.C.5
-
12
-
-
0033059723
-
-
For examples of Sonogashira coupling, see: (a) Dai, W.-M.; Wu, J.; Fong, K. C.; Lee, M. Y. H.; Lau, C. W. J. Org. Chem. 1999, 64, 5062-5082.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5062-5082
-
-
Dai, W.-M.1
Wu, J.2
Fong, K.C.3
Lee, M.Y.H.4
Lau, C.W.5
-
18
-
-
0028003698
-
-
For an example of the intramolecular Heck reaction, see: Toyota, M.; Nishikawa, Y.; Fukumoto, K. Tetrahedron 1994, 50, 11153-11166.
-
(1994)
Tetrahedron
, vol.50
, pp. 11153-11166
-
-
Toyota, M.1
Nishikawa, Y.2
Fukumoto, K.3
-
19
-
-
0021915012
-
-
For an example of bromohydroxylation/amination en route to α-methylene-γ-lactams, see: Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385.
-
(1985)
Tetrahedron
, vol.41
, pp. 375-385
-
-
Mori, M.1
Chiba, K.2
Okita, M.3
Kayo, I.4
Ban, Y.5
-
20
-
-
0033540691
-
-
As a source of functionalized vinyllithium and vinylcuprate reagents, see: Cloninger, M. J.; Overman, L.-E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 1092-1093
-
-
Cloninger, M.J.1
Overman, L.-E.2
-
21
-
-
0033603829
-
-
(b) As a source of vinylstannanes, see: Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600-7605.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7600-7605
-
-
Han, X.1
Stoltz, B.M.2
Corey, E.J.3
-
23
-
-
84970567689
-
-
(d) For an example of oxidation to α-bromo enones, see: Della, E. W.; Pigou, P. E. Aust. J. Chem. 1983, 36, 2261-2268.
-
(1983)
Aust. J. Chem.
, vol.36
, pp. 2261-2268
-
-
Della, E.W.1
Pigou, P.E.2
-
26
-
-
0034618249
-
-
(f) For an example of Mitsunobu aminodehydroxylation, see: Murphy, J. A.; Scott, K. A.; Sinclair, R. S.; Martin, C. G.; Kennedy, A. R.; Lewis, N. J. Chem. Soc., Perkin Trans. 1 2000, 2395-2408.
-
(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 2395-2408
-
-
Murphy, J.A.1
Scott, K.A.2
Sinclair, R.S.3
Martin, C.G.4
Kennedy, A.R.5
Lewis, N.6
-
28
-
-
28744448466
-
-
(h) For examples of dehydrobromination to the corresponding propargyl alcohol, see: Lespieau, R. C.R. Hebd. Seances Acad. Sci. 1911, 152, 879-881.
-
(1911)
C.R. Hebd. Seances Acad. Sci.
, vol.152
, pp. 879-881
-
-
Lespieau, R.1
-
31
-
-
0027318462
-
-
(b) Nagasawa, K.; Ishihara, H.; Zako, Y.; Shimizu, I. J. Org. Chem. 1993, 58, 2523-2529.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 2523-2529
-
-
Nagasawa, K.1
Ishihara, H.2
Zako, Y.3
Shimizu, I.4
-
34
-
-
0001039697
-
-
Smith, A. B.; Levenberg, P. A.; Jerris, P. J.; Scarborough, R. M.; Wovkulich, P. M. J. Am. Chem. Soc. 1981, 103, 1501-1513.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 1501-1513
-
-
Smith, A.B.1
Levenberg, P.A.2
Jerris, P.J.3
Scarborough, R.M.4
Wovkulich, P.M.5
-
35
-
-
37049088684
-
-
Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzalez, A. M.; Pulido, F. J.; Rubio, R. J. Chem. Soc., Perkin Trans. 1 1993, 1657-1662.
-
(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 1657-1662
-
-
Barbero, A.1
Cuadrado, P.2
Fleming, I.3
Gonzalez, A.M.4
Pulido, F.J.5
Rubio, R.6
-
36
-
-
0000936473
-
-
2 = Me; 50% yield), see: Sandler, S. R. J. Org. Chem. 1967, 32, 3876-3881.
-
(1967)
J. Org. Chem.
, vol.32
, pp. 3876-3881
-
-
Sandler, S.R.1
-
38
-
-
64149085162
-
-
Sydnes, L. K.; Hemmingsen, T. H. Acta Chem. Scand., Ser. B 1985, 39, 93-102.
-
(1985)
Acta Chem. Scand., Ser. B
, vol.39
, pp. 93-102
-
-
Sydnes, L.K.1
Hemmingsen, T.H.2
-
40
-
-
0000464892
-
-
Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 4984-4985
-
-
Tamao, K.1
Maeda, K.2
Yamaguchi, T.3
Ito, Y.4
-
43
-
-
0001360021
-
-
Campos, P. J.; Sampedro, D.; Rodriguez, M. A. Organometallics 1998, 17, 5390-5396.
-
(1998)
Organometallics
, vol.17
, pp. 5390-5396
-
-
Campos, P.J.1
Sampedro, D.2
Rodriguez, M.A.3
-
45
-
-
0013402838
-
-
Shimizu, N.; Shibata, F.; Tsuno, Y. Bull. Chem. Soc. Jpn. 1987, 60, 777-778.
-
(1987)
Bull. Chem. Soc. Jpn.
, vol.60
, pp. 777-778
-
-
Shimizu, N.1
Shibata, F.2
Tsuno, Y.3
-
48
-
-
0141629754
-
-
A preliminary account of some of these studies has appeared in: Novikov, Y. Y.; Sampson, P. Org. Lett. 2003, 5, 2263-2266.
-
(2003)
Org. Lett.
, vol.5
, pp. 2263-2266
-
-
Novikov, Y.Y.1
Sampson, P.2
-
50
-
-
28744456223
-
-
note
-
The Trapp mixture is THF, ether, and pentane (4:1:1 by volume). This mixture has a sufficiently low viscosity at -110 to -115 °C to provide a useful reaction medium.
-
-
-
-
51
-
-
28744442092
-
-
University of Minnesota: Minneapolis, MN
-
Xidos, J. D.; Li, J.; Zhu, T.; Hawkins, G. D.; Thompson, J. D.; Chuang, Y.-Y.; Fast, P. L.; Liotard, D. A.; Rinaldi, D.; Cramer, C. J.; Truhlar, D. G. GAMESSPLUS, version 3.9; University of Minnesota: Minneapolis, MN, 2003.
-
(2003)
GAMESSPLUS, Version 3.9
-
-
Xidos, J.D.1
Li, J.2
Zhu, T.3
Hawkins, G.D.4
Thompson, J.D.5
Chuang, Y.-Y.6
Fast, P.L.7
Liotard, D.A.8
Rinaldi, D.9
Cramer, C.J.10
Truhlar, D.G.11
-
52
-
-
84893169025
-
-
Based on the General Atomic and Molecular Electronic Structure System (GAMESS) as described in: Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
-
(1993)
J. Comput. Chem.
, vol.14
, pp. 1347-1363
-
-
Schmidt, M.W.1
Baldridge, K.K.2
Boatz, J.A.3
Elbert, S.T.4
Gordon, M.S.5
Jensen, J.H.6
Koseki, S.7
Matsunaga, N.8
Nguyen, K.A.9
Su, S.J.10
Windus, T.L.11
Dupuis, M.12
Montgomery, J.A.13
-
53
-
-
0000251142
-
-
Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1995, 117, 2297-2300.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 2297-2300
-
-
Lucchini, V.1
Modena, G.2
Pasquato, L.3
-
56
-
-
0030043567
-
-
Thoma, G.; Schwarzenbach, F.; Duthalet, R. O. J. Org. Chem. 1996, 61, 514-524.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 514-524
-
-
Thoma, G.1
Schwarzenbach, F.2
Duthalet, R.O.3
-
57
-
-
0016184979
-
-
Miljkovic, M.; Gligorijevic, M.; Satoh, T.; Miljkovic, D. J. Org. Chem. 1974, 39, 1379-1384.
-
(1974)
J. Org. Chem.
, vol.39
, pp. 1379-1384
-
-
Miljkovic, M.1
Gligorijevic, M.2
Satoh, T.3
Miljkovic, D.4
-
58
-
-
28744452983
-
-
note
-
Of course, the α-anomer would suffer increased steric crowding on the α-face, which might have eroded this high stereocontrol; unfortunately, no studies along these lines have been published.
-
-
-
-
59
-
-
0033118841
-
-
Davis, B. G.; Nash, R. J.; Watson, A. A.; Smith, C.; Fleet, G. W. Tetrahedron 1999, 14, 4501-4520.
-
(1999)
Tetrahedron
, vol.14
, pp. 4501-4520
-
-
Davis, B.G.1
Nash, R.J.2
Watson, A.A.3
Smith, C.4
Fleet, G.W.5
-
61
-
-
84988115972
-
-
For reviews on the use of acylsilanes in organic synthesis, see: (a) Ricci, A.; Deglinnocenti, A. Synthesis 1989, 647-660.
-
(1989)
Synthesis
, pp. 647-660
-
-
Ricci, A.1
Deglinnocenti, A.2
-
62
-
-
0000634803
-
-
(b) Bulman-Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
-
(1990)
Chem. Soc. Rev.
, vol.19
, pp. 147-195
-
-
Bulman-Page, P.C.1
Klair, S.S.2
Rosenthal, S.3
-
63
-
-
0001598940
-
-
(c) Bonini, B. F.; Franchini, M. C.; Fochi, M. Gazz. Chim. Ital. 1997, 127, 619-628.
-
(1997)
Gazz. Chim. Ital.
, vol.127
, pp. 619-628
-
-
Bonini, B.F.1
Franchini, M.C.2
Fochi, M.3
-
64
-
-
0000790187
-
-
(d) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A. J. Organomet. Chem. 1998, 567, 181-189.
-
(1998)
J. Organomet. Chem.
, vol.567
, pp. 181-189
-
-
Bonini, B.F.1
Comes-Franchini, M.2
Fochi, M.3
Mazzanti, G.4
Ricci, A.5
-
66
-
-
0021386867
-
-
Kato, M.; Mori, A.; Oshino, H.; Enda, J.; Kobayashi, K.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1773-1778.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 1773-1778
-
-
Kato, M.1
Mori, A.2
Oshino, H.3
Enda, J.4
Kobayashi, K.5
Kuwajima, I.6
-
67
-
-
3643118528
-
-
A very limited number of α-halo-α-silyl ketones have previously been reported, (a) For an example of Hal = Br, Cl, see: Berti, G.; Canedoli, S.; Crotti, P.; Macchia, F. J. Chem. Soc., Perkin Trans. 1 1984, 1183-1188.
-
(1984)
J. Chem. Soc., Perkin Trans. 1
, pp. 1183-1188
-
-
Berti, G.1
Canedoli, S.2
Crotti, P.3
Macchia, F.4
-
68
-
-
0035179062
-
-
(b) For an example of Hal = F, see: Enders, D.; Faure, S.; Potthoff, M.; Runsink, J. Synthesis 2001, 2307-2319.
-
(2001)
Synthesis
, pp. 2307-2319
-
-
Enders, D.1
Faure, S.2
Potthoff, M.3
Runsink, J.4
-
69
-
-
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-
-
note
-
A typical optimization took about 3 weeks on a desktop 2.4 GHz Pentium 4 computer with 1 GB memory; this precluded the use of an MP2 correlation correction as well as HF/DFT methods available within the GAMESOL package.
-
-
-
-
72
-
-
37049088684
-
-
Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzalez, A. M.; Pulido, F. J.; Rubio, R. J. Chem. Soc., Perkin Trans. 1 1993, 1657-1662.
-
(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 1657-1662
-
-
Barbero, A.1
Cuadrado, P.2
Fleming, I.3
Gonzalez, A.M.4
Pulido, F.J.5
Rubio, R.6
-
73
-
-
0030943222
-
-
Singleton, D. A.; Leung, S.-W.; Martinez, J. P.; Lee, Y.-K. Tetrahedron Lett. 1997, 38, 3163-3166.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3163-3166
-
-
Singleton, D.A.1
Leung, S.-W.2
Martinez, J.P.3
Lee, Y.-K.4
-
74
-
-
28744456783
-
-
The closely related 1-bromo-1-chloroethene was mentioned in the literature (Havel, J. J.; Skell, P. S. J. Am. Chem. Soc. 1972, 94, 1792-1793.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 1792-1793
-
-
Havel, J.J.1
Skell, P.S.2
-
76
-
-
0038384658
-
-
but it readily polymerizes and has not found utility as a synthetic reagent. In contrast, 1,1-dichloroethene is an inexpensive article of commerce, and has found some synthetic utility. For an example, see: Qian, M.; Negishi, E. Org. Process Res. Dev. 2003, 7, 412-417.
-
(2003)
Org. Process Res. Dev.
, vol.7
, pp. 412-417
-
-
Qian, M.1
Negishi, E.2
-
77
-
-
2542584805
-
-
For examples, see: (a) Qian, M.; Huang, Z.; Negishi, E. Org. Lett. 2004, 6, 1531-1534.
-
(2004)
Org. Lett.
, vol.6
, pp. 1531-1534
-
-
Qian, M.1
Huang, Z.2
Negishi, E.3
-
78
-
-
4444284414
-
-
(b) Haleh, G.; Antunes, L. M.; Organ, M. G. Org. Lett. 2004, 6, 2913-2916.
-
(2004)
Org. Lett.
, vol.6
, pp. 2913-2916
-
-
Haleh, G.1
Antunes, L.M.2
Organ, M.G.3
-
79
-
-
0343145647
-
-
Krief, A.; Vos, M. J.; Lombart, S.; Bosret, J.; Couty, F. Tetrahedron Lett. 1997, 38, 6295-6298.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 6295-6298
-
-
Krief, A.1
Vos, M.J.2
Lombart, S.3
Bosret, J.4
Couty, F.5
-
80
-
-
0021915012
-
-
Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385.
-
(1985)
Tetrahedron
, vol.41
, pp. 375-385
-
-
Mori, M.1
Chiba, K.2
Okita, M.3
Kayo, I.4
Ban, Y.5
-
82
-
-
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-
-
note
-
The preparation of 8a is presented in the Supporting Information.
-
-
-
-
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-
-
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note
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Ketone 9a was kindly provided by Dr. Peter Norris, Department of Chemistry, Youngstown State University.
-
-
-
-
84
-
-
0038278406
-
-
Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 4772-4783
-
-
Torrente, S.1
Noya, B.2
Branchadell, V.3
Alonso, R.4
-
86
-
-
0033591112
-
-
Lattanzi, A.; Sagulo, F.; Scettri, A. Tetrahedron: Asymmetry 1999, 10, 2023-2036.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 2023-2036
-
-
Lattanzi, A.1
Sagulo, F.2
Scettri, A.3
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