-
4
-
-
34848848499
-
-
(b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886.
-
(2007)
Science
, vol.317
, pp. 1881-1886
-
-
Müller, K.1
Faeh, C.2
Diederich, F.3
-
5
-
-
38149070200
-
-
(c) 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
-
7
-
-
34547677638
-
-
For a review of strategies for trifluoromethylation, see
-
For a review of strategies for trifluoromethylation, see: Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975-996.
-
(2007)
J. Fluorine Chem
, vol.128
, pp. 975-996
-
-
Ma, J.-A.1
Cahard, D.2
-
8
-
-
58149357724
-
-
For reviews of asymmetric trifluoromethylations, see: a
-
For reviews of asymmetric trifluoromethylations, see: (a) Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43.
-
(2008)
Chem. Rev
, vol.108
-
-
Ma, J.-A.1
Cahard, D.2
-
9
-
-
58349091443
-
-
(b) Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633-2644.
-
(2008)
Tetrahedron: Asymmetry
, vol.19
, pp. 2633-2644
-
-
Shibata, N.1
Mizuta, S.2
Kawai, H.3
-
11
-
-
0006598557
-
-
For seminal contributions towards the nucleophilic trifluoromethylation of carbonyls, see: a
-
For seminal contributions towards the nucleophilic trifluoromethylation of carbonyls, see: (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
-
12
-
-
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
-
15
-
-
0001548395
-
-
(e) Ait-Mohand, S.; Takechi, N.; Médebielle, M.; Dolbier, W. R., Jr. Org. Lett. 2001, 3, 4271-4273.
-
(2001)
Org. Lett
, vol.3
, pp. 4271-4273
-
-
Ait-Mohand, S.1
Takechi, N.2
Médebielle, M.3
Dolbier Jr., W.R.4
-
16
-
-
0001529255
-
-
For seminal contributions towards the electrophilic or radical trifluoromethylation of enamines, enolates, and other carbonyl derivatives, see: a
-
For seminal contributions towards the electrophilic or radical trifluoromethylation of enamines, enolates, and other carbonyl derivatives, see: (a) Cantacuzène, D.; Dorme, R. Tetrahedron Lett. 1975, 16, 2031-2034.
-
(1975)
Tetrahedron Lett
, vol.16
, pp. 2031-2034
-
-
Cantacuzène, D.1
Dorme, R.2
-
17
-
-
0025119619
-
-
(b) Miura, K.; Taniguchi, M.; Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6391-6394.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 6391-6394
-
-
Miura, K.1
Taniguchi, M.2
Nozaki, K.3
Oshima, K.4
Utimoto, K.5
-
21
-
-
33846525992
-
-
(f) Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754-757.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 754-757
-
-
Kieltsch, I.1
Eisenberger, P.2
Togni, A.3
-
22
-
-
65949090286
-
-
(g) Sato, K.; Yuki, T.; Yamaguchi, R.; Hamano, T.; Tarui, A.; Omote, M.; Kumadaki, I.; Ando, A. J. Org. Chem. 2009, 74, 3815-3819.
-
(2009)
J. Org. Chem
, vol.74
, pp. 3815-3819
-
-
Sato, K.1
Yuki, T.2
Yamaguchi, R.3
Hamano, T.4
Tarui, A.5
Omote, M.6
Kumadaki, I.7
Ando, A.8
-
23
-
-
33845376895
-
-
For examples of moderately stereoselective methods, see: (a) Kitazume, T, Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186-5191
-
For examples of moderately stereoselective methods, see: (a) Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186-5191.
-
-
-
-
26
-
-
38349100690
-
-
(a) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569.
-
(2007)
Chem. Rev
, vol.107
, pp. 5471-5569
-
-
Mukherjee, S.1
Yang, J.W.2
Hoffmann, S.3
List, B.4
-
29
-
-
67650283342
-
-
For recent examples of photoredox catalysis applications in organic synthesis, see: a
-
For recent examples of photoredox catalysis applications in organic synthesis, see: (a) Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886-12887.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 12886-12887
-
-
Ischay, M.A.1
Anzovino, M.E.2
Du, J.3
Yoon, T.P.4
-
31
-
-
67649625293
-
-
(c) Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756-8757.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 8756-8757
-
-
Narayanam, J.M.R.1
Tucker, J.W.2
Stephenson, C.R.J.3
-
32
-
-
70349895886
-
-
DOI: 10.1002/anie.200901603
-
(d) Müller, C.; Bauer, A.; Bach, T. Angew. Chem., Int. Ed. 2009, 48, DOI: 10.1002/anie.200901603.
-
(2009)
Angew. Chem., Int. Ed
, vol.48
-
-
Müller, C.1
Bauer, A.2
Bach, T.3
-
34
-
-
68249156113
-
-
Although Ir(ppy)2(dtb-bpy)PF6 1 was optimal for this transformation, commercially available Ru(bpy)3Cl 2 could also be used to afford the desired products in slightly diminished yields and enantioselectivities (Table 1, entry 5, 1 is available in a single step from commercially available [Ir(ppy) 2Cl]2 Sigma-Aldrich, CAS-No 92220-65-0, See ref 12
-
2 (Sigma-Aldrich, CAS-No 92220-65-0). See ref 12.
-
-
-
-
35
-
-
1542287638
-
-
6 1, see: Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763-2767.
-
6 1, see: Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763-2767.
-
-
-
-
36
-
-
34547840326
-
-
For a review on the photoproperties of iridium complexes, see
-
For a review on the photoproperties of iridium complexes, see: Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143-203.
-
(2007)
Top. Curr. Chem
, vol.281
, pp. 143-203
-
-
Flamigni, L.1
Barbieri, A.2
Sabatini, C.3
Ventura, B.4
Barigelletti, F.5
-
37
-
-
68249159089
-
-
6, Stern-Volmer constant = 185; see Supporting Information for details.
-
6, Stern-Volmer constant = 185; see Supporting Information for details.
-
-
-
-
38
-
-
0025071071
-
-
(a) Andrieux, C. P.; Gelis, L.; Médebielle, M.; Pinson, J.; Saveant, J. M. J. Am. Chem. Soc. 1990, 112, 3509-3520.
-
(1990)
J. Am. Chem. Soc
, vol.112
, pp. 3509-3520
-
-
Andrieux, C.P.1
Gelis, L.2
Médebielle, M.3
Pinson, J.4
Saveant, J.M.5
-
40
-
-
0001194619
-
-
Wayner, D. D. M.; Dannenberg, J. J.; Griller, D. Chem. Phys. Lett. 1986, 131, 189-191.
-
(1986)
Chem. Phys. Lett
, vol.131
, pp. 189-191
-
-
Wayner, D.D.M.1
Dannenberg, J.J.2
Griller, D.3
-
41
-
-
68249147019
-
-
Performed using B3LYP/6-311+G(2d,p)//B3LYP/6-31Gd, See ref 9
-
Performed using B3LYP/6-311+G(2d,p)//B3LYP/6-31G(d). See ref 9.
-
-
-
-
42
-
-
70349904562
-
-
We have recently shown the disruption of a postreaction racemization pathway via design of catalyst 2 versus catalyst 10, see: Amatore, M, Beeson, T. D, Brown, S. P, MacMillan, D. W. C. Angew. Chem, Int. Ed. 2009, 48, 5121-5124
-
We have recently shown the disruption of a postreaction racemization pathway via design of catalyst 2 (versus catalyst 10); see: Amatore, M.; Beeson, T. D.; Brown, S. P.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2009, 48, 5121-5124.
-
-
-
-
43
-
-
68249157553
-
-
3 formyl adduct was observed at room temperature but not at -20°C.
-
3 formyl adduct was observed at room temperature but not at -20°C.
-
-
-
-
44
-
-
68249160251
-
-
Lower reaction efficiency appears to lead to lower enantiopurity as the product is exposed to unconsumed base i.e, Table 1, entry 5, catalyst 9
-
Lower reaction efficiency appears to lead to lower enantiopurity as the product is exposed to unconsumed base (i.e., Table 1, entry 5, catalyst 9).
-
-
-
-
45
-
-
68249152894
-
-
A hitherto unreported amine catalyst 11 was employed in entry 7 (Table 2); see Supporting Information.
-
A hitherto unreported amine catalyst 11 was employed in entry 7 (Table 2); see Supporting Information.
-
-
-
-
46
-
-
68249140885
-
-
19F NMR yield); however facile postreaction racemization is observed.
-
19F NMR yield); however facile postreaction racemization is observed.
-
-
-
-
47
-
-
68249157552
-
-
2 and MeOH to afford β-trifluoromethyl alcohols in high yield and enantioselectivity.
-
2 and MeOH to afford β-trifluoromethyl alcohols in high yield and enantioselectivity.
-
-
-
|