-
1
-
-
0242526099
-
-
For recent reviews of C-H activation, see
-
For recent reviews of C-H activation, see: Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
-
(2003)
Adv. Synth. Catal.
, vol.345
, pp. 1077
-
-
Kakiuchi, F.1
Chatani, N.2
-
5
-
-
33846918696
-
-
Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
-
(2007)
Chem. Rev.
, vol.107
, pp. 174
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
7
-
-
67649488045
-
-
Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 5094
-
-
Chen, X.1
Engle, K.M.2
Wang, D.-H.3
Yu, J.-Q.4
-
8
-
-
77149164746
-
-
Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
-
(2010)
Chem.-Eur. J.
, vol.16
, pp. 2654
-
-
Jazzar, R.1
Hitce, J.2
Renaudat, A.3
Sofack-Kreutzer, J.4
Baudoin, O.5
-
9
-
-
24644495100
-
-
For selected recent references, see
-
For selected recent references, see: Pastine, S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005, 127, 12180
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 12180
-
-
Pastine, S.J.1
McQuaid, K.M.2
Sames, D.3
-
11
-
-
33746302757
-
-
Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 1683
-
-
Tobisu, M.1
Chatani, N.2
-
12
-
-
33746905548
-
-
Bajracharya, G. B.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 6204
-
(2006)
J. Org. Chem.
, vol.71
, pp. 6204
-
-
Bajracharya, G.B.1
Pahadi, N.K.2
Gridnev, I.D.3
Yamamoto, Y.4
-
13
-
-
53249123367
-
-
Barluenga, J.; Fananás-Mastral, M.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2008, 47, 6594
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6594
-
-
Barluenga, J.1
Fananás-Mastral, M.2
Aznar, F.3
Valdés, C.4
-
15
-
-
67749142078
-
-
Shikanai, D.; Murase, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2009, 131, 3166
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3166
-
-
Shikanai, D.1
Murase, H.2
Hata, T.3
Urabe, H.4
-
16
-
-
68049099258
-
-
Tobisu, M.; Nakai, H.; Chatani, N. J. Org. Chem. 2009, 74, 5471
-
(2009)
J. Org. Chem.
, vol.74
, pp. 5471
-
-
Tobisu, M.1
Nakai, H.2
Chatani, N.3
-
17
-
-
70349783659
-
-
Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009, 48, 3999
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 3999
-
-
Yang, S.1
Li, Z.2
Jian, X.3
He, C.4
-
18
-
-
67649342031
-
-
Mahoney, S. J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50, 4706
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4706
-
-
Mahoney, S.J.1
Moon, D.T.2
Hollinger, J.3
Fillion, E.4
-
20
-
-
77951158758
-
-
Mori, K.; Kawasaki, T.; Sueoka, S.; Akiyama, T. Org. Lett. 2010, 12, 1732
-
(2010)
Org. Lett.
, vol.12
, pp. 1732
-
-
Mori, K.1
Kawasaki, T.2
Sueoka, S.3
Akiyama, T.4
-
21
-
-
77949395209
-
-
Jurberg, I. D.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 3543
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3543
-
-
Jurberg, I.D.1
Odabachian, Y.2
Gagosz, F.3
-
23
-
-
79952271674
-
-
Mori, K.; Sueoka, S.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 2424
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 2424
-
-
Mori, K.1
Sueoka, S.2
Akiyama, T.3
-
24
-
-
77957065022
-
-
These types of reactions have been classified under the term tert -amino effect. For reviews, see
-
These types of reactions have been classified under the term tert -amino effect. For reviews, see: Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl. Chem. 1972, 14, 211
-
(1972)
Adv. Heterocycl. Chem.
, vol.14
, pp. 211
-
-
Meth-Cohn, O.1
Suschitzky, H.2
-
28
-
-
33748291386
-
-
Matyus, P.; Elias, O.; Tapolcsanyi, P.; Polonka-Balint, A.; Halasz-Dajka, B. Synthesis 2006, 2625
-
(2006)
Synthesis
, pp. 2625
-
-
Matyus, P.1
Elias, O.2
Tapolcsanyi, P.3
Polonka-Balint, A.4
Halasz-Dajka, B.5
-
29
-
-
0020782543
-
-
Reinhoudt, D. N.; Visser, G. W.; Verboom, W.; Benders, P. H.; Pennings, M. L. M. J. Am. Chem. Soc. 1983, 105, 4775-4781
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 4775-4781
-
-
Reinhoudt, D.N.1
Visser, G.W.2
Verboom, W.3
Benders, P.H.4
Pennings, M.L.M.5
-
30
-
-
0344626623
-
-
Verboom, W.; Reinhoudt, D. N.; Visser, R.; Harkema, S. J. Org. Chem. 1984, 49, 269
-
(1984)
J. Org. Chem.
, vol.49
, pp. 269
-
-
Verboom, W.1
Reinhoudt, D.N.2
Visser, R.3
Harkema, S.4
-
31
-
-
0012118604
-
-
Nijhuis, W. H. N.; Verboom, W.; Reinhoudt, D. N.; Harkema, S. J. Am. Chem. Soc. 1987, 109, 3136
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 3136
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Reinhoudt, D.N.3
Harkema, S.4
-
33
-
-
0010338271
-
-
Groenen, L. C.; Verboom, W.; Nijhuis, W. H. N.; Reinhoudt, D. N.; Van Hummel, G. J.; Feil, D. Tetrahedron 1988, 44, 4637
-
(1988)
Tetrahedron
, vol.44
, pp. 4637
-
-
Groenen, L.C.1
Verboom, W.2
Nijhuis, W.H.N.3
Reinhoudt, D.N.4
Van Hummel, G.J.5
Feil, D.6
-
34
-
-
0024597364
-
-
Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 199
-
(1989)
J. Org. Chem.
, vol.54
, pp. 199
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Abu El-Fadl, A.3
Harkema, S.4
Reinhoudt, D.N.5
-
35
-
-
0024489430
-
-
Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Van Hummel, G. J.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 209
-
(1989)
J. Org. Chem.
, vol.54
, pp. 209
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Abu El-Fadl, A.3
Van Hummel, G.J.4
Reinhoudt, D.N.5
-
36
-
-
0028284171
-
-
De Boeck, B.; Jiang, S.; Janousek, Z.; Viehe, H. G. Tetrahedron 1994, 50, 7075
-
(1994)
Tetrahedron
, vol.50
, pp. 7075
-
-
De Boeck, B.1
Jiang, S.2
Janousek, Z.3
Viehe, H.G.4
-
37
-
-
0028882631
-
-
De Boeck, B.; Janousek, Z.; Viehe, H. G. Tetrahedron 1995, 51, 13239
-
(1995)
Tetrahedron
, vol.51
, pp. 13239
-
-
De Boeck, B.1
Janousek, Z.2
Viehe, H.G.3
-
38
-
-
0032576855
-
-
Ojea, V.; Muinelo, I.; Quintela, J. M. Tetrahedron 1998, 54, 927
-
(1998)
Tetrahedron
, vol.54
, pp. 927
-
-
Ojea, V.1
Muinelo, I.2
Quintela, J.M.3
-
39
-
-
23944461239
-
-
Kaval, N.; Halasz-Dajka, B.; Vo-Thanh, G.; Dehaen, W.; Van der Eycken, J.; Matyus, P.; Loupy, A.; Van der Eycken, E. Tetrahedron 2005, 61, 9052
-
(2005)
Tetrahedron
, vol.61
, pp. 9052
-
-
Kaval, N.1
Halasz-Dajka, B.2
Vo-Thanh, G.3
Dehaen, W.4
Van Der Eycken, J.5
Matyus, P.6
Loupy, A.7
Van Der Eycken, E.8
-
40
-
-
40149096724
-
-
Zhang, C.; Kanta De, C.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 416
-
-
Zhang, C.1
De Kanta, C.2
Mal, R.3
Seidel, D.4
-
41
-
-
56849106003
-
-
Polonka-Bálint, A.; Saraceno, C.; Ludányi, K.; Bényei, A.; Mátyus, P. Synlett 2008, 2846
-
(2008)
Synlett
, pp. 2846
-
-
Polonka-Bálint, A.1
Saraceno, C.2
Ludányi, K.3
Bényei, A.4
Mátyus, P.5
-
42
-
-
59649112358
-
-
Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129
-
(2009)
Org. Lett.
, vol.11
, pp. 129
-
-
Murarka, S.1
Zhang, C.2
Konieczynska, M.D.3
Seidel, D.4
-
43
-
-
67749147313
-
-
Ruble, J. C.; Hurd, A. R.; Johnson, T. A.; Sherry, D. A.; Barbachyn, M. R.; Toogood, P. L.; Bundy, G. L.; Graber, D. R.; Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 3991
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3991
-
-
Ruble, J.C.1
Hurd, A.R.2
Johnson, T.A.3
Sherry, D.A.4
Barbachyn, M.R.5
Toogood, P.L.6
Bundy, G.L.7
Graber, D.R.8
Kamilar, G.M.9
-
44
-
-
67650311554
-
-
McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972
-
(2009)
Org. Lett.
, vol.11
, pp. 2972
-
-
McQuaid, K.M.1
Long, J.Z.2
Sames, D.3
-
45
-
-
77956053142
-
-
Földi, A. A.; Ludányi, K.; Bényei, A. C.; Mátyus, P. Synlett 2010, 2109
-
(2010)
Synlett
, pp. 2109
-
-
Földi, A.A.1
Ludányi, K.2
Bényei, A.C.3
Mátyus, P.4
-
46
-
-
77349092323
-
-
Dunkel, P.; Túrós, D.; Bényei, A.; Ludányi, K.; Mátyus, P. Tetrahedron 2010, 66, 2331
-
(2010)
Tetrahedron
, vol.66
, pp. 2331
-
-
Dunkel, P.1
Túrós, D.2
Bényei, A.3
Ludányi, K.4
Mátyus, P.5
-
47
-
-
77957673072
-
-
Alajarin, M.; Bonillo, B.; Ortin, M.-M.; Sanchez-Andrada, P.; Vidal, A.; Orenes, R.-A. Org. Biomol. Chem. 2010, 8, 4690
-
(2010)
Org. Biomol. Chem.
, vol.8
, pp. 4690
-
-
Alajarin, M.1
Bonillo, B.2
Ortin, M.-M.3
Sanchez-Andrada, P.4
Vidal, A.5
Orenes, R.-A.6
-
48
-
-
70450169585
-
-
For other types of internal redox reactions, see
-
For other types of internal redox reactions, see: Pahadi, N. K.; Paley, M.; Jana, R.; Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2009, 131, 16626
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 16626
-
-
Pahadi, N.K.1
Paley, M.2
Jana, R.3
Waetzig, S.R.4
Tunge, J.A.5
-
51
-
-
79951830781
-
-
Zhang, C.; Das, D.; Seidel, D. Chem. Sci. 2011, 2, 233
-
(2011)
Chem. Sci.
, vol.2
, pp. 233
-
-
Zhang, C.1
Das, D.2
Seidel, D.3
-
52
-
-
67650473037
-
-
Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T. Chem. Lett. 2009, 38, 524
-
(2009)
Chem. Lett.
, vol.38
, pp. 524
-
-
Mori, K.1
Ohshima, Y.2
Ehara, K.3
Akiyama, T.4
-
53
-
-
52949141872
-
-
For Brønsted acid-catalyzed internal redox reactions, see
-
For Brønsted acid-catalyzed internal redox reactions, see: Che, X.; Sheng, L.; Dang, Q.; Bai, X. Synlett 2008, 2373
-
(2008)
Synlett
, pp. 2373
-
-
Che, X.1
Sheng, L.2
Dang, Q.3
Bai, X.4
-
54
-
-
58149293587
-
-
Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009, 74, 419
-
(2009)
J. Org. Chem.
, vol.74
, pp. 419
-
-
Zhang, C.1
Murarka, S.2
Seidel, D.3
-
55
-
-
79951841771
-
-
Haibach, M. C.; Deb, I.; Kanta De, C.; Seidel, D. J. Am. Chem. Soc. 2011, 133, 2100
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 2100
-
-
Haibach, M.C.1
Deb, I.2
De Kanta, C.3
Seidel, D.4
-
56
-
-
2342570203
-
-
Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1566
-
-
Akiyama, T.1
Itoh, J.2
Yokota, K.3
Fuchibe, K.4
-
58
-
-
33745683617
-
-
For reviews of chiral phosphoric acid catalysis, see
-
For reviews of chiral phosphoric acid catalysis, see: Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 999
-
-
Akiyama, T.1
Itoh, J.2
Fuchibe, K.3
-
62
-
-
78149432679
-
-
Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. M. Org. Biomol. Chem. 2010, 8, 5262
-
(2010)
Org. Biomol. Chem.
, vol.8
, pp. 5262
-
-
Zamfir, A.1
Schenker, S.2
Freund, M.3
Tsogoeva, S.M.4
-
63
-
-
77953261329
-
-
references cited therein
-
Terada, M. Synthesis 2010, 1929 and references cited therein
-
(2010)
Synthesis
, pp. 1929
-
-
Terada, M.1
-
64
-
-
70349399209
-
-
Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 13226
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 13226
-
-
Murarka, S.1
Deb, I.2
Zhang, C.3
Seidel, D.4
-
65
-
-
77956081347
-
-
Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 11847
-
-
Kang, Y.K.1
Kim, S.M.2
Kim, D.Y.3
-
66
-
-
79951649015
-
-
Cao, W.; Liu, X.; Wang, W.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 600
-
(2011)
Org. Lett.
, vol.13
, pp. 600
-
-
Cao, W.1
Liu, X.2
Wang, W.3
Lin, L.4
Feng, X.5
-
67
-
-
79952133884
-
-
Zhou, G.; Liu, F.; Zhang, J. Chem.-Eur. J. 2011, 17, 3101
-
(2011)
Chem.-Eur. J.
, vol.17
, pp. 3101
-
-
Zhou, G.1
Liu, F.2
Zhang, J.3
-
68
-
-
79955014658
-
-
For the detailed screening of catalysts and substrates, see the Supporting Information
-
For the detailed screening of catalysts and substrates, see the Supporting Information.
-
-
-
-
69
-
-
79955015011
-
-
Substrates possessing an N-cyclic moiety such as an isoquinoline, isoindoline, pyrrolidine, or piperidine ring yielded low enantioselectivities (less than 10% ee)
-
Substrates possessing an N-cyclic moiety such as an isoquinoline, isoindoline, pyrrolidine, or piperidine ring yielded low enantioselectivities (less than 10% ee).
-
-
-
-
70
-
-
79954985859
-
-
Phosphoric acid derivatives 5 and 6 were used after washing with 6 N HCl
-
Phosphoric acid derivatives 5 and 6 were used after washing with 6 N HCl.
-
-
-
-
71
-
-
79955023765
-
-
The absolute configuration of (S)- 8 was determined by X-ray analysis of the corresponding monobrominated product s30. For more details, see the Supporting Information
-
The absolute configuration of (S)- 8 was determined by X-ray analysis of the corresponding monobrominated product s30. For more details, see the Supporting Information.
-
-
-
-
72
-
-
79955011703
-
-
In the 1980s, the Reinhoudt group found the thermal version of the highly stereoselective internal redox reaction. In their case, the chiral information of the starting material was completely converted into the cyclized product. For more details, see refs 3e, 4c, and 4g
-
In the 1980s, the Reinhoudt group found the thermal version of the highly stereoselective internal redox reaction. In their case, the chiral information of the starting material was completely converted into the cyclized product. For more details, see refs 3e, 4c, and 4g.
-
-
-
-
73
-
-
0345022255
-
-
This kind of asymmetric transformation is recognized as memory of chirality . For leading references, see
-
This kind of asymmetric transformation is recognized as memory of chirality . For leading references, see: Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 9694
-
-
Kawabata, T.1
Yahiro, K.2
Fuji, K.3
-
76
-
-
79955041173
-
-
The significant decrease in the enantioselectivity when (R)- 7 was used implies the existence of matched and mismatched modes in the cyclization step. The reason for this stereomutation is unclear and under investigation
-
The significant decrease in the enantioselectivity when (R)- 7 was used implies the existence of matched and mismatched modes in the cyclization step. The reason for this stereomutation is unclear and under investigation.
-
-
-
-
77
-
-
79954987191
-
-
Treatment of (S)- 7 with rac -binaphthyl phosphoric acid 6a afforded (S)- 8 with 85% ee, although the chemical yield was low (15%). We also tried the achiral acid catalyst (biphenyl phosphoric acid). Although high temperature and a longer reaction time were required (in toluene at refluxing temperature for 68 h), the stereochemical information was retained at an acceptable level. The cyclized adduct (S)-8 was obtained with 54% ee in 40% chemical yield. For more details, see the Supporting Information
-
Treatment of (S)- 7 with rac -binaphthyl phosphoric acid 6a afforded (S)- 8 with 85% ee, although the chemical yield was low (15%). We also tried the achiral acid catalyst (biphenyl phosphoric acid). Although high temperature and a longer reaction time were required (in toluene at refluxing temperature for 68 h), the stereochemical information was retained at an acceptable level. The cyclized adduct (S)-8 was obtained with 54% ee in 40% chemical yield. For more details, see the Supporting Information.
-
-
-
-
78
-
-
79955032405
-
-
Seidel (10a) and Feng (10c) proposed that enantiofacial selection of the iminium cation is the key factor leading to the high enantioselectivity
-
Seidel (10a) and Feng (10c) proposed that enantiofacial selection of the iminium cation is the key factor leading to the high enantioselectivity.
-
-
-
-
79
-
-
38749146550
-
-
3)-hydrogen takes place in metal-catalyzed enantioselective nitrene or carbenoid insertion reactions. For selected recent references, see
-
3)-hydrogen takes place in metal-catalyzed enantioselective nitrene or carbenoid insertion reactions. For selected recent references, see: Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
-
(2008)
Nature
, vol.451
, pp. 417
-
-
Davies, H.M.L.1
Manning, J.R.2
-
80
-
-
53249096011
-
-
Milczek, E.; Boudet, N.; Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6825
-
-
Milczek, E.1
Boudet, N.2
Blakey, S.3
-
82
-
-
79955002677
-
-
The key [1,5]-hydride shift took place suprafacially. For more details, see refs 4c and 4g and references cited therein
-
The key [1,5]-hydride shift took place suprafacially. For more details, see refs 4c and 4g and references cited therein.
-
-
-
|