-
4
-
-
38149016915
-
-
and references therein
-
O'Hagan, D Chem. Soc. Rev 2008, 37, 308-319, and references therein.
-
(2008)
Chem. Soc. Rev
, vol.37
, pp. 308-319
-
-
O'Hagan, D.1
-
5
-
-
4544369746
-
-
For reviews on fluorinated molecules in medicinal chemistry and agrochemistry, see: a
-
For reviews on fluorinated molecules in medicinal chemistry and agrochemistry, see: (a) Jeschke, P. ChemBioChem 2004, 5, 570-589.
-
(2004)
ChemBioChem
, vol.5
, pp. 570-589
-
-
Jeschke, P.1
-
6
-
-
4444355871
-
-
(b) Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-640.
-
(2004)
ChemBioChem
, vol.5
, pp. 637-640
-
-
Böhm, H.-J.1
Banner, D.2
Bendels, S.3
Kansy, M.4
Kuhn, B.5
Müller, K.6
Obst-Sander, U.7
Stahl, M.8
-
12
-
-
38149070200
-
-
(h) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330.
-
(2008)
Chem. Soc. Rev
, vol.37
, pp. 320-330
-
-
Purser, S.1
Moore, P.R.2
Swallow, S.3
Gouverneur, V.4
-
14
-
-
0006598557
-
-
(a) Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 25, 2195-2198.
-
(1984)
Tetrahedron Lett
, vol.25
, pp. 2195-2198
-
-
Ruppert, I.1
Schlich, K.2
Volbach, W.3
-
15
-
-
33845183108
-
-
(b) Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393-395.
-
(1989)
J. Am. Chem. Soc
, vol.111
, pp. 393-395
-
-
Prakash, G.K.S.1
Krishnamurti, R.2
Olah, G.A.3
-
16
-
-
0031140114
-
-
For reviews on nucleophilic trifluoromethylation, see: a
-
For reviews on nucleophilic trifluoromethylation, see: (a) Prakash, G. K. S.; Yudin, K. Chem. Rev. 1997, 97, 757-786.
-
(1997)
Chem. Rev
, vol.97
, pp. 757-786
-
-
Prakash, G.K.S.1
Yudin, K.2
-
22
-
-
0032889876
-
-
(a) Nelson, D. W.; Easley, R. A.; Pintea, B. N. V. Tetrahedron Lett. 1999, 40, 25-28.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 25-28
-
-
Nelson, D.W.1
Easley, R.A.2
Pintea, B.N.V.3
-
23
-
-
0035917368
-
-
(b) Nelson, D. W.; Owens, J.; Hiraldo, D. J. Org. Chem. 2001, 66, 2572-2582.
-
(2001)
J. Org. Chem
, vol.66
, pp. 2572-2582
-
-
Nelson, D.W.1
Owens, J.2
Hiraldo, D.3
-
24
-
-
17144431832
-
-
(a) Mukaiyama, T.; Kawano, Y.; Fujisawa, H. Chem. Lett. 2005, 34, 88-89.
-
(2005)
Chem. Lett
, vol.34
, pp. 88-89
-
-
Mukaiyama, T.1
Kawano, Y.2
Fujisawa, H.3
-
25
-
-
19444383265
-
-
(b) Kawano, Y.; Fujisawa, H.; Mukaiyama, T. Chem. Lett. 2005, 34, 422-423.
-
(2005)
Chem. Lett
, vol.34
, pp. 422-423
-
-
Kawano, Y.1
Fujisawa, H.2
Mukaiyama, T.3
-
26
-
-
33750589376
-
-
(c) Kawano, Y.; Kaneko, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2006, 79, 1133-1145.
-
(2006)
Bull. Chem. Soc. Jpn
, vol.79
, pp. 1133-1145
-
-
Kawano, Y.1
Kaneko, N.2
Mukaiyama, T.3
-
27
-
-
33750021972
-
-
Prakash, G. K. S.; Panja, C.; Vaghoo, H.; Surampudi, V.; Kultyshev, R.; Mandal, M.; Rasul, G.; Mathew, T.; Olah, G. A. J. Org. Chem. 2006, 71, 6806-6813.
-
(2006)
J. Org. Chem
, vol.71
, pp. 6806-6813
-
-
Prakash, G.K.S.1
Panja, C.2
Vaghoo, H.3
Surampudi, V.4
Kultyshev, R.5
Mandal, M.6
Rasul, G.7
Mathew, T.8
Olah, G.A.9
-
28
-
-
0042786801
-
-
Prakash, G. K. S.; Mandal, M.; Panja, C.; Mathew, T.; Olah, G. A. J. Fluorine Chem. 2003, 133, 61-63.
-
(2003)
J. Fluorine Chem
, vol.133
, pp. 61-63
-
-
Prakash, G.K.S.1
Mandal, M.2
Panja, C.3
Mathew, T.4
Olah, G.A.5
-
29
-
-
32344446963
-
-
(a) Mizuta, S.; Shibata, N.; Sato, T.; Fujimoto, H.; Nakamura, S.; Toru, T. Synlett 2006, 267-270.
-
(2006)
Synlett
, pp. 267-270
-
-
Mizuta, S.1
Shibata, N.2
Sato, T.3
Fujimoto, H.4
Nakamura, S.5
Toru, T.6
-
31
-
-
20444472366
-
-
Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193-2196.
-
(2005)
Org. Lett
, vol.7
, pp. 2193-2196
-
-
Song, J.J.1
Tan, Z.2
Reeves, J.T.3
Gallou, F.4
Yee, N.K.5
Senanayake, C.H.6
-
32
-
-
85013587834
-
-
3, etc. have also been described but with low yields; see: Hagiwara, T.; Kobayashi, T.; Fuchikami, T. Main Group Chem. 1997, 2, 13-15.
-
3, etc. have also been described but with low yields; see: Hagiwara, T.; Kobayashi, T.; Fuchikami, T. Main Group Chem. 1997, 2, 13-15.
-
-
-
-
33
-
-
33745223065
-
-
Mizuta, S.; Shibata, N.; Ogawa, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Chem. Commun. 2006, 2575-2577.
-
(2006)
Chem. Commun
, pp. 2575-2577
-
-
Mizuta, S.1
Shibata, N.2
Ogawa, S.3
Fujimoto, H.4
Nakamura, S.5
Toru, T.6
-
34
-
-
0028332523
-
-
(a) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35, 3137-3138.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 3137-3138
-
-
Iseki, K.1
Nagai, T.2
Kobayashi, Y.3
-
35
-
-
0042739225
-
-
(b) Caron, S.; Do, N. M.; Arpin, P.; Larivée, A. Synthesis 2003, 1693-1698.
-
(2003)
Synthesis
, pp. 1693-1698
-
-
Caron, S.1
Do, N.M.2
Arpin, P.3
Larivée, A.4
-
36
-
-
34250194606
-
-
(c) Nagao, H.; Yamane, Y.; Mukaiyama, T. Chem. Lett. 2007, 36, 666-667.
-
(2007)
Chem. Lett
, vol.36
, pp. 666-667
-
-
Nagao, H.1
Yamane, Y.2
Mukaiyama, T.3
-
37
-
-
45249091767
-
-
(d) Nagao, H.; Kawano, Y.; Mukaiyama, T. Bull Chem. Soc. Jpn. 2007, 80, 2406-2412.
-
(2007)
Bull Chem. Soc. Jpn
, vol.80
, pp. 2406-2412
-
-
Nagao, H.1
Kawano, Y.2
Mukaiyama, T.3
-
38
-
-
34548535299
-
-
(e) Mizuta, S.; Shibata, N.; Akiti, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Org. Lett. 2007, 9, 3707-3710.
-
(2007)
Org. Lett
, vol.9
, pp. 3707-3710
-
-
Mizuta, S.1
Shibata, N.2
Akiti, S.3
Fujimoto, H.4
Nakamura, S.5
Toru, T.6
-
39
-
-
33644653856
-
-
(a) Pedrosa, R.; Sayalero, S.; Vicente, M.: Maestro, A. J. Org. Chem. 2006, 71, 2177-2180.
-
(2006)
J. Org. Chem
, vol.71
, pp. 2177-2180
-
-
Pedrosa, R.1
Sayalero, S.2
Vicente, M.3
Maestro, A.4
-
41
-
-
33846113396
-
-
(c) Song, J. J.; Tan, Z.; Xu, J.; Reeves, J. T.; Yee, N. K.; Ramdas, R.; Gallou, F.; Kuzmich, K.; DeLattre, L.; Lee, H.; Feng, X.; Senanayake, C. H. J. Org. Chem. 2007, 72, 292-294.
-
(2007)
J. Org. Chem
, vol.72
, pp. 292-294
-
-
Song, J.J.1
Tan, Z.2
Xu, J.3
Reeves, J.T.4
Yee, N.K.5
Ramdas, R.6
Gallou, F.7
Kuzmich, K.8
DeLattre, L.9
Lee, H.10
Feng, X.11
Senanayake, C.H.12
-
42
-
-
33846958448
-
-
(d) Massicot, F.; Monnier-Benoit, N.; Deka, N.; Plantier-Royon, R.; Portella, C. J. Org. Chem. 2007, 72, 1174-1180.
-
(2007)
J. Org. Chem
, vol.72
, pp. 1174-1180
-
-
Massicot, F.1
Monnier-Benoit, N.2
Deka, N.3
Plantier-Royon, R.4
Portella, C.5
-
46
-
-
37549027127
-
-
For examples of total synthesis of natural products from tartaric acid derived ketoamides, see: Prasad, K. R, Gholap, S. L. J. Org. Chem. 2008, 73, 2-11, and references therein
-
For examples of total synthesis of natural products from tartaric acid derived ketoamides, see: Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2008, 73, 2-11, and references therein.
-
-
-
-
47
-
-
0029896691
-
-
Nugiel, D. A.; Jacobs, K.; Worley, T.; Patel, M; Kaltenbach, R. F.; Meyer, D. T.; Jadhav, P. K.: DeLucca, G. V.; Smyser, T. E.; Klabe, R. M.; Bacheler, L. T.; Rayner, M. M.; Seitz, S. P. J. Med. Chem. 1996, 39, 2156-2169.
-
(1996)
J. Med. Chem
, vol.39
, pp. 2156-2169
-
-
Nugiel, D.A.1
Jacobs, K.2
Worley, T.3
Patel, M.4
Kaltenbach, R.F.5
Meyer, D.T.6
Jadhav, P.K.7
DeLucca, G.V.8
Smyser, T.E.9
Klabe, R.M.10
Bacheler, L.T.11
Rayner, M.M.12
Seitz, S.P.13
-
49
-
-
33751384950
-
-
Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182-6189.
-
(1993)
J. Org. Chem
, vol.58
, pp. 6182-6189
-
-
Kondo, Y.1
Green, J.R.2
Ho, J.3
-
50
-
-
0035855341
-
-
(a) McNulty, J.; Grunner, V.; Mao, J. Tetrahedron Lett. 2001, 42, 5609-5612.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 5609-5612
-
-
McNulty, J.1
Grunner, V.2
Mao, J.3
-
52
-
-
0033515608
-
-
3 leading exclusively to α-hydroxy α- trifluoromethylated amides, see: Singh, R. J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579-2581.
-
3 leading exclusively to α-hydroxy α- trifluoromethylated amides, see: Singh, R. J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2579-2581.
-
-
-
-
53
-
-
53849099514
-
-
3 in the presence of a catalytic amount of fluoride gave the corresponding hemiaminal: Monnier-Benoit, N.; Massicot, F.; Portella, C. unpublished results. (Chemical Equation Presented)
-
3 in the presence of a catalytic amount of fluoride gave the corresponding hemiaminal: Monnier-Benoit, N.; Massicot, F.; Portella, C. unpublished results. (Chemical Equation Presented)
-
-
-
-
54
-
-
0000601499
-
-
2O, see: Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. J. Am. Chem. Soc. 1990, 112, 7619-7625.
-
2O, see: Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. J. Am. Chem. Soc. 1990, 112, 7619-7625.
-
-
-
-
57
-
-
0000251474
-
-
3 in DMF, see:Stahly, G. P.; Bell, D. R. J. Org. Chem. 1989, 54, 2873-2877.
-
3 in DMF, see:Stahly, G. P.; Bell, D. R. J. Org. Chem. 1989, 54, 2873-2877.
-
-
-
-
59
-
-
1542527758
-
-
For various methodologies for converting silyl ethers into alkyl ethers, see: a
-
For various methodologies for converting silyl ethers into alkyl ethers, see: (a) Edwards, L. H.; Turner, C. E.; Thames, S. F. Tetrahedron Lett. 1969, 48, 4225-4228.
-
(1969)
Tetrahedron Lett
, vol.48
, pp. 4225-4228
-
-
Edwards, L.H.1
Turner, C.E.2
Thames, S.F.3
-
60
-
-
0012929464
-
-
(b) Sinhababu, A. K.; Kawase, M.; Borchardt, R. T. Tetrahedron Lett. 1987, 28, 4139-4142.
-
(1987)
Tetrahedron Lett
, vol.28
, pp. 4139-4142
-
-
Sinhababu, A.K.1
Kawase, M.2
Borchardt, R.T.3
-
61
-
-
33845282062
-
-
(c) Sassaman, M. B.; Kotian, K. D.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1987, 52, 4314-4319.
-
(1987)
J. Org. Chem
, vol.52
, pp. 4314-4319
-
-
Sassaman, M.B.1
Kotian, K.D.2
Prakash, G.K.S.3
Olah, G.A.4
-
65
-
-
0028023376
-
-
(a) Bennani, Y. L.; Vanhessche, K. P. M.; Sharpless, K. B. Tetrahedron: Asymmetry 1994, 5, 1473-1476.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1473-1476
-
-
Bennani, Y.L.1
Vanhessche, K.P.M.2
Sharpless, K.B.3
-
66
-
-
0037458693
-
-
(b) Moreno-Dorado, F. J.; Guerra, F. M.; Ortega, M. J.; Zubia, E.; Massanet, G. M. Tetrahedron: Asymmetry 2003, 14, 503-510.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 503-510
-
-
Moreno-Dorado, F.J.1
Guerra, F.M.2
Ortega, M.J.3
Zubia, E.4
Massanet, G.M.5
-
67
-
-
0037423340
-
-
Vutukuri, D. R.; Bharathi, P.; Yu, Z.; Rajasekaran, K.; Tran, M.-H.; Thayumanavan, S. J. Org. Chem. 2003, 68, 1146-1149.
-
(2003)
J. Org. Chem
, vol.68
, pp. 1146-1149
-
-
Vutukuri, D.R.1
Bharathi, P.2
Yu, Z.3
Rajasekaran, K.4
Tran, M.-H.5
Thayumanavan, S.6
-
68
-
-
53849138975
-
-
A procedure similar to the one reported in the Experimental Section for the millimolar scale was applied, except for the purification of the ketoamide 5 and the intermediate (R)-13, which was carried out by crystallization instead of flash chromatography (crystallization solvents were petroleum ether/Et2O for 5, petroleum ether for (R)-13
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2O for 5, petroleum ether for (R)-13).
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