-
4
-
-
33646468489
-
-
For recent reviews, see: Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 1520
-
-
Taylor, M.S.1
Jacobsen, E.N.2
-
7
-
-
16844374787
-
-
For recent reviews, see: Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 1924
-
-
Yamamoto, H.1
Futatsugi, K.2
-
8
-
-
21544444468
-
-
Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491
-
(2005)
Synlett
, pp. 1491
-
-
Kanai, M.1
Kato, N.2
Ichikawa, E.3
Shibasaki, M.4
-
11
-
-
68949170991
-
-
Shibasaki, M.; Kanai, M.; Matsunaga, S.; Kumagai, N. Acc. Chem. Res. 2009, 42, 1117
-
(2009)
Acc. Chem. Res.
, vol.42
, pp. 1117
-
-
Shibasaki, M.1
Kanai, M.2
Matsunaga, S.3
Kumagai, N.4
-
14
-
-
44649177050
-
-
For recent reviews, see: Paull, D. H.; Abraham, C. J.; Scerba, M. T.; Alden-Danforth, E.; Lectka, T. Acc. Chem. Res. 2008, 41, 655
-
(2008)
Acc. Chem. Res.
, vol.41
, pp. 655
-
-
Paull, D.H.1
Abraham, C.J.2
Scerba, M.T.3
Alden-Danforth, E.4
Lectka, T.5
-
16
-
-
77955808773
-
-
Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
-
(2010)
Chem.-Eur. J.
, vol.16
, pp. 9350
-
-
Rueping, M.1
Koenigs, R.M.2
Atodiresei, I.3
-
19
-
-
27444443731
-
-
Taylor, M. S.; Tokunaga, N.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 6700
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 6700
-
-
Taylor, M.S.1
Tokunaga, N.2
Jacobsen, E.N.3
-
20
-
-
35948942795
-
-
Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 13404
-
-
Raheem, I.T.1
Thiara, P.S.2
Peterson, E.A.3
Jacobsen, E.N.4
-
21
-
-
44949230317
-
-
Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 7198
-
-
Reisman, S.E.1
Doyle, A.G.2
Jacobsen, E.N.3
-
22
-
-
70349914539
-
-
Peterson, E. A.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2009, 48, 6328
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6328
-
-
Peterson, E.A.1
Jacobsen, E.N.2
-
24
-
-
77950805314
-
-
Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 5030
-
-
Knowles, R.R.1
Lin, S.2
Jacobsen, E.N.3
-
25
-
-
77957343192
-
-
Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 7332
-
-
Veitch, G.E.1
Jacobsen, E.N.2
-
27
-
-
0034599654
-
-
Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 1279
-
-
Sigman, M.S.1
Vachal, P.2
Jacobsen, E.N.3
-
29
-
-
0000728050
-
-
Su, J. T.; Vachal, P.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 197
-
(2001)
Adv. Synth. Catal.
, vol.343
, pp. 197
-
-
Su, J.T.1
Vachal, P.2
Jacobsen, E.N.3
-
30
-
-
70350055059
-
-
Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968
-
(2009)
Nature
, vol.461
, pp. 968
-
-
Zuend, S.J.1
Coughlin, M.P.2
Lalonde, M.P.3
Jacobsen, E.N.4
-
32
-
-
77149152524
-
-
Xu, A.; Zuend, S. J.; Woll, M. G.; Jacobsen, E. N. Science 2010, 327, 986
-
(2010)
Science
, vol.327
, pp. 986
-
-
Xu, A.1
Zuend, S.J.2
Woll, M.G.3
Jacobsen, E.N.4
-
36
-
-
49349100124
-
-
Weil, T.; Kotke, M.; Kleiner, C. M.; Schreiner, P. R. Org. Lett. 2008, 10, 1513
-
(2008)
Org. Lett.
, vol.10
, pp. 1513
-
-
Weil, T.1
Kotke, M.2
Kleiner, C.M.3
Schreiner, P.R.4
-
37
-
-
72249110249
-
-
De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 17060
-
-
De, C.K.1
Klauber, E.G.2
Seidel, D.3
-
38
-
-
77957323978
-
-
Klauber, E. G.; De, C. K.; Shar, T. K.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 13624
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 13624
-
-
Klauber, E.G.1
De, C.K.2
Shar, T.K.3
Seidel, D.4
-
39
-
-
77956473421
-
-
For a recent review, see: Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235
-
(2010)
Chem. Rev.
, vol.110
, pp. 5235
-
-
Gulevich, A.V.1
Zhdanko, A.G.2
Orru, R.V.A.3
Nenajdenko, V.G.4
-
40
-
-
33845376099
-
-
For Au(I) catalysis, see:, For a Ag(I) catalysis, see: Tetrahedron Lett. 1991, 32, 2799 For a comprehensive review, see: ref 13.
-
For Au(I) catalysis, see: Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405 For a Ag(I) catalysis, see: Hayashi, T.; Uozumi, Y.; Yamazaki, A. Tetrahedron Lett. 1991, 32, 2799 For a comprehensive review, see: ref 13.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6405
-
-
Ito, Y.1
Sawamura, M.2
Hayashi, T.3
Hayashi, T.4
Uozumi, Y.5
Yamazaki, A.6
-
41
-
-
0001058494
-
-
Nesper, R.; Pregosin, P. S.; Püntener, K.; Wörle, M. Helv. Chim. Acta 1993, 76, 2239
-
(1993)
Helv. Chim. Acta
, vol.76
, pp. 2239
-
-
Nesper, R.1
Pregosin, P.S.2
Püntener, K.3
Wörle, M.4
-
42
-
-
0000240922
-
-
Gorla, F.; Togni, A.; Venanzi, L. M.; Albinati, A.; Lianza, F. Organometallics 1994, 13, 1607
-
(1994)
Organometallics
, vol.13
, pp. 1607
-
-
Gorla, F.1
Togni, A.2
Venanzi, L.M.3
Albinati, A.4
Lianza, F.5
-
43
-
-
0001286113
-
-
Longmire, J. M.; Zhang, X.; Shang, M. Organometallics 1998, 17, 4374
-
(1998)
Organometallics
, vol.17
, pp. 4374
-
-
Longmire, J.M.1
Zhang, X.2
Shang, M.3
-
44
-
-
0013220379
-
-
Motoyama, Y.; Kawakami, H.; Shimozono, K.; Aoki, K.; Nishiyama, H. Organometallics 2002, 21, 3408
-
(2002)
Organometallics
, vol.21
, pp. 3408
-
-
Motoyama, Y.1
Kawakami, H.2
Shimozono, K.3
Aoki, K.4
Nishiyama, H.5
-
45
-
-
33645871616
-
-
Gosiewska, S.; Huisin't Vald, M.; de Pater, J. J. M.; Bruijnincx, P. C. A.; Lutz, M.; Spek, A. L.; van Koten, G.; Klein Gebbink, R. J. M. Tetrahedron: Asymmetry 2006, 17, 674
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 674
-
-
Gosiewska, S.1
Huisin'T Vald, M.2
De Pater, J.J.M.3
Bruijnincx, P.C.A.4
Lutz, M.5
Spek, A.L.6
Van Koten, G.7
Klein Gebbink, R.J.M.8
-
46
-
-
45449110456
-
-
Gosiewska, S.; Herreras, S. M.; Lutz, M.; Spek, A. L.; Havenith, R. W. A.; van Klink, G. P. M.; van Koten, G.; Klein Gebbink, R. J. M. Organometallics 2008, 27, 2549
-
(2008)
Organometallics
, vol.27
, pp. 2549
-
-
Gosiewska, S.1
Herreras, S.M.2
Lutz, M.3
Spek, A.L.4
Havenith, R.W.A.5
Van Klink, G.P.M.6
Van Koten, G.7
Klein Gebbink, R.J.M.8
-
48
-
-
51949105875
-
-
Li, L.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 12248
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 12248
-
-
Li, L.1
Klauber, E.G.2
Seidel, D.3
-
49
-
-
72149086659
-
-
Shi, Z.; Yu, P.; Chua, P. J.; Zhong, G. Adv. Synth. Catal. 2009, 351, 2797
-
(2009)
Adv. Synth. Catal.
, vol.351
, pp. 2797
-
-
Shi, Z.1
Yu, P.2
Chua, P.J.3
Zhong, G.4
-
50
-
-
77950207491
-
-
Jiang, X.; Zhang, G.; Fu, D.; Cao, Y.; Shen, F.; Wang, R. Org. Lett. 2010, 12, 1544
-
(2010)
Org. Lett.
, vol.12
, pp. 1544
-
-
Jiang, X.1
Zhang, G.2
Fu, D.3
Cao, Y.4
Shen, F.5
Wang, R.6
-
54
-
-
79952591348
-
-
See the Supporting Information for more details.
-
See the Supporting Information for more details.
-
-
-
-
55
-
-
70349928914
-
-
Kim, H. Y.; Shih, H.-J.; Knabe, W. E.; Oh, K. Angew. Chem., Int. Ed. 2009, 48, 7420
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 7420
-
-
Kim, H.Y.1
Shih, H.-J.2
Knabe, W.E.3
Oh, K.4
-
57
-
-
77953675884
-
-
Kim, H. Y.; Kim, S.; Oh, K. Angew. Chem., Int. Ed. 2010, 49, 4476
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 4476
-
-
Kim, H.Y.1
Kim, S.2
Oh, K.3
-
58
-
-
79952600616
-
-
2) resulted in catalysts with low enantioselectivities.
-
2) resulted in catalysts with low enantioselectivities.
-
-
-
-
59
-
-
0003998388
-
-
Typical ionic radius for Cu(I) with a coordination number of 4 is 0.60 Å, whereas that of Co(II) is around 0.56 Å see:, 87 th ed.; CRC: Boca Raton, FL
-
Typical ionic radius for Cu(I) with a coordination number of 4 is 0.60 Å, whereas that of Co(II) is around 0.56 Å see: Handbook of Chemistry and Physics, 87 th ed.; CRC: Boca Raton, FL, 2006; pp 12 - 11.
-
(2006)
Handbook of Chemistry and Physics
, pp. 12-11
-
-
-
60
-
-
77950462376
-
-
2NEt), but metal iodides require amidine bases (i.e., DBU); see: Ref 19. A cooperative role of amidine bases in the asymmetric Co(II) catalysis has been recently reported; see: Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 3268
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3268
-
-
Kalow, J.A.1
Doyle, A.G.2
-
61
-
-
79952610749
-
-
Use of other metal salts and modified thiourea derivatives is currently under investigation.
-
Use of other metal salts and modified thiourea derivatives is currently under investigation.
-
-
-
-
62
-
-
0035907043
-
-
3N, see
-
3N, see: Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 1884
-
-
Evans, D.A.1
Janey, J.M.2
Magomedov, N.3
Tedrow, J.S.4
-
63
-
-
79952578533
-
-
The anion-binding of thioureas to isocyanides under our cooperative catalysis could not be confirmed by NMR or IR due to the line-broadening caused by the multifunctional nature of our chiral metal complexes. However, our control experiments (Table 1, entries 14-17) clearly indicate the cooperative role of thiourea derivatives on enantioselectivity.
-
The anion-binding of thioureas to isocyanides under our cooperative catalysis could not be confirmed by NMR or IR due to the line-broadening caused by the multifunctional nature of our chiral metal complexes. However, our control experiments (Table 1, entries 14-17) clearly indicate the cooperative role of thiourea derivatives on enantioselectivity.
-
-
-
-
64
-
-
0001361008
-
-
Tetrahedral Co(II) complexes are known to be blue, and octahedral Co(II) complexes are usually pink; see: Norwood, V. M., III; Morse, K. W. Inorg. Chem. 1987, 26, 284
-
(1987)
Inorg. Chem.
, vol.26
, pp. 284
-
-
Norwood III, V.M.1
Morse, K.W.2
-
65
-
-
1642480108
-
-
Romerosa, A.; Saraiba-Bello, C.; Serrano-Ruiz, M.; Caneschi, A.; McKee, V.; Peruzzini, M.; Sorace, L.; Zanobini, F. J. Chem. Soc., Dalton Trans. 2003, 3233
-
(2003)
J. Chem. Soc., Dalton Trans.
, pp. 3233
-
-
Romerosa, A.1
Saraiba-Bello, C.2
Serrano-Ruiz, M.3
Caneschi, A.4
McKee, V.5
Peruzzini, M.6
Sorace, L.7
Zanobini, F.8
-
66
-
-
79952589499
-
-
Oxazolines were isolated in <10% yields after 48 h (>20:1 dr and 5% ee).
-
Oxazolines were isolated in <10% yields after 48 h (>20:1 dr and 5% ee).
-
-
-
-
67
-
-
79952582637
-
-
-) provided racemic anti- 3a in 71% yield and 10:1 dr.
-
-) provided racemic anti- 3a in 71% yield and 10:1 dr.
-
-
-
|