-
2
-
-
23044486219
-
-
(a) Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 4682
-
-
Denmark, S.E.1
Heemstra Jr., J.R.2
Beutner, G.L.3
-
3
-
-
0033690703
-
-
(b) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
-
(2000)
Chem. Rev
, vol.100
, pp. 1929
-
-
Casiraghi, G.1
Zanardi, F.2
Appendino, G.3
Rassu, G.4
-
6
-
-
34247884846
-
-
Trost, B. M, Fleming, L. Eds, Pergamon Press: Oxford, Chapters 1.1-1.6. pp
-
Comprehensive Organic Synthesis; Trost, B. M., Fleming, L. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapters 1.1-1.6. pp 1-268.
-
(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1-268
-
-
-
9
-
-
0030902124
-
-
(c) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. 1997, 36, 186.
-
(1997)
Angew. Chem., Int. Ed
, vol.36
, pp. 186
-
-
Krause, N.1
Gerold, A.2
-
13
-
-
0000679263
-
-
Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin, Chapter 31, pp
-
(c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 3, Chapter 31, pp 1105-1142.
-
(1999)
Comprehensive Asymmetric Catalysis
, vol.3
, pp. 1105-1142
-
-
-
14
-
-
0003544583
-
-
2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim, Germany
-
(d) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 569.
-
(2000)
Catalytic Asymmetric Synthesis
, pp. 569
-
-
Kanai, M.1
Shibasaki, M.2
-
16
-
-
0037065336
-
-
See, for example: a
-
See, for example: (a) Ohshima, T.; Xu, Y.; Takita, R.; Shimizu, S.; Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 14546
-
-
Ohshima, T.1
Xu, Y.2
Takita, R.3
Shimizu, S.4
Zhong, D.5
Shibasaki, M.6
-
17
-
-
33645455231
-
-
(b) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 3928
-
-
Wang, Y.1
Liu, X.2
Deng, L.3
-
18
-
-
33646049727
-
-
(c) Van Summeren, R. P.; Moody, D. B.; Feringa, B. L.; Minnaard, A. J. J. Am. Chem. Soc. 2006, 128, 4546.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 4546
-
-
Van Summeren, R.P.1
Moody, D.B.2
Feringa, B.L.3
Minnaard, A.J.4
-
19
-
-
0347129770
-
-
(d) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 96
-
-
Cesati III, R.R.1
de Armas, J.2
Hoveyda, A.H.3
-
20
-
-
33746277828
-
-
(e) Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. Angew. Chem., Int. Ed. 2006, 45, 4635.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 4635
-
-
Shibuguchi, T.1
Mihara, H.2
Kuramochi, A.3
Sakuraba, S.4
Ohshima, T.5
Shibasaki, M.6
-
21
-
-
33746290813
-
-
(f) Brandau, S.; Landa, A.; Franzén, J.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 4305
-
-
Brandau, S.1
Landa, A.2
Franzén, J.3
Marigo, M.4
Jørgensen, K.A.5
-
23
-
-
0001428047
-
-
(b) Corey, E. J.; Kim, C. U.; Chen, R. H. K.; Takeda, M. J. Am. Chem. Soc. 1972, 94, 4395.
-
(1972)
J. Am. Chem. Soc
, vol.94
, pp. 4395
-
-
Corey, E.J.1
Kim, C.U.2
Chen, R.H.K.3
Takeda, M.4
-
24
-
-
0035907847
-
-
(c) Canisius, J.; Mobley, T. A.; Berger, S.; Krause, N. Chem. - Eur. J. 2001, 7, 2671.
-
(2001)
Chem. - Eur. J
, vol.7
, pp. 2671
-
-
Canisius, J.1
Mobley, T.A.2
Berger, S.3
Krause, N.4
-
26
-
-
33747229725
-
-
(e) Nishimura, T.; Yasuhara, Y.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 5164.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 5164
-
-
Nishimura, T.1
Yasuhara, Y.2
Hayashi, T.3
-
27
-
-
29444458959
-
-
(f) de la Herrán, G.; Murcia, C.; Csáky, A. G. Org. Lett. 2005, 7, 5629.
-
(2005)
Org. Lett
, vol.7
, pp. 5629
-
-
de la Herrán, G.1
Murcia, C.2
Csáky, A.G.3
-
29
-
-
22144458723
-
-
(a) Hayashi, T.; Yamamoto, S.; Tokunaga, N. Angew. Chem., Int. Ed. 2005, 44, 4224.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 4224
-
-
Hayashi, T.1
Yamamoto, S.2
Tokunaga, N.3
-
30
-
-
0842285210
-
-
(b) Hayashi, T.; Tokunaga, N.; Inoue, K. Org. Lett. 2004, 6, 305.
-
(2004)
Org. Lett
, vol.6
, pp. 305
-
-
Hayashi, T.1
Tokunaga, N.2
Inoue, K.3
-
31
-
-
33845211504
-
-
(c) Fillon, E.; Wilsily, A.; Liao, E.-T. Tetrahedron: Asymmetry 2006, 17, 2957.
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 2957
-
-
Fillon, E.1
Wilsily, A.2
Liao, E.-T.3
-
32
-
-
0039260128
-
-
See, for example: a
-
See, for example: (a) Kohler, E. P.; Butler, F. R. J. Am. Chem. Soc. 1926, 48, 1036.
-
(1926)
J. Am. Chem. Soc
, vol.48
, pp. 1036
-
-
Kohler, E.P.1
Butler, F.R.2
-
33
-
-
34247871816
-
-
(b) Danishefsky, S.; Koppel, G.; Levine, R. Tetrahedron Lett. 1968, 9, 2257.
-
(1968)
Tetrahedron Lett
, vol.9
, pp. 2257
-
-
Danishefsky, S.1
Koppel, G.2
Levine, R.3
-
34
-
-
0011224648
-
-
(c) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410.
-
(1973)
J. Am. Chem. Soc
, vol.95
, pp. 2410
-
-
Danishefsky, S.1
Hatch, W.E.2
Sax, M.3
Abola, E.4
Pletcher, J.5
-
36
-
-
0035955854
-
-
(e) Ballini, R.; Bosica, G.; Fiorini, D. Tetrahedron Lett. 2001, 42, 8471.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 8471
-
-
Ballini, R.1
Bosica, G.2
Fiorini, D.3
-
38
-
-
0035886887
-
-
See, e.g, a
-
See, e.g.: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 3726
-
-
Dalko, P.I.1
Moisan, L.2
-
39
-
-
6044269452
-
-
(b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
-
(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 5138
-
-
Dalko, P.I.1
Moisan, L.2
-
40
-
-
47749122232
-
-
Berkessel, A, Gröger, H, Eds, Wiley-VCH: Weinheim, Germany
-
(c) Asymmetric Organocatalysis; Berkessel, A., Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
-
(2005)
Asymmetric Organocatalysis
-
-
-
41
-
-
0003544583
-
-
2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim, Germany
-
(a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 727.
-
(2000)
Catalytic Asymmetric Synthesis
, pp. 727
-
-
O'Donnell, M.J.1
-
42
-
-
0002855131
-
-
Vogtle, F, Stoddard, J. F, Shibasaki, M, Eds, Wiley-VCH: Weinheim, Germany
-
(b) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F., Stoddard, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000; p 123.
-
(2000)
Stimulating Concepts in Chemistry
, pp. 123
-
-
Shioiri, T.1
Arai, S.2
-
43
-
-
0032490960
-
-
For asymmetric PTC transformations of β-ketoesters, see: a
-
For asymmetric PTC transformations of β-ketoesters, see: (a) Manabe, K. Tetrahedron Lett. 1998, 39, 5807.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 5807
-
-
Manabe, K.1
-
45
-
-
0036317692
-
-
(c) Dehmlov, E. V.; Düttmann, S.; Neumann, B.; Stammler, H.-G. Eur. J. Org. Chem. 2002, 2087.
-
(2002)
Eur. J. Org. Chem
, pp. 2087
-
-
Dehmlov, E.V.1
Düttmann, S.2
Neumann, B.3
Stammler, H.-G.4
-
46
-
-
0041363231
-
-
(d) Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 3796.
-
(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 3796
-
-
Ooi, T.1
Miki, T.2
Taniguchi, M.3
Shiraishi, M.4
Takeuchi, M.5
Maruoka, K.6
-
47
-
-
4644351571
-
-
(e) Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897.
-
(2004)
J. Org. Chem
, vol.69
, pp. 6897
-
-
Park, E.J.1
Kim, M.H.2
Kim, D.Y.3
-
48
-
-
15744377645
-
-
(f) Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 3670
-
-
Bella, M.1
Kobbelgaard, S.2
Jørgensen, K.A.3
-
49
-
-
33745450163
-
-
(g) Kobbelgaard, S.; Bella, M.; Jørgensen, K. A. J. Org. Chem. 2006, 71, 4980.
-
(2006)
J. Org. Chem
, vol.71
, pp. 4980
-
-
Kobbelgaard, S.1
Bella, M.2
Jørgensen, K.A.3
-
50
-
-
33749827801
-
-
(g) Poulsen, T. B.; Bernardi, L.; Bell, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 6551.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 6551
-
-
Poulsen, T.B.1
Bernardi, L.2
Bell, M.3
Jørgensen, K.A.4
-
51
-
-
33846220324
-
-
(h) Poulsen, T. B.; Bernardi, L.; Alemán, J.; Overgaard, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2007, 129, 441.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 441
-
-
Poulsen, T.B.1
Bernardi, L.2
Alemán, J.3
Overgaard, J.4
Jørgensen, K.A.5
-
52
-
-
0002076066
-
-
For reviews on the use of 2 for asymmetric transformations under PTC, see: (a) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
-
For reviews on the use of 2 for asymmetric transformations under PTC, see: (a) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
-
-
-
-
57
-
-
0000234063
-
-
(b) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 12414
-
-
Corey, E.J.1
Xu, F.2
Noe, M.C.3
-
59
-
-
34247899502
-
-
2O-promoted dehydration (see the Supporting Information).
-
2O-promoted dehydration (see the Supporting Information).
-
-
-
-
62
-
-
34247880794
-
-
This model was developed on the basis of an X-ray crystallographic analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 12h
-
This model was developed on the basis of an X-ray crystallographic analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 12h.
-
-
-
-
63
-
-
0001866893
-
-
For a review on the synthesis and applications of bicyclo[3.2.1]octanes, see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
-
For a review on the synthesis and applications of bicyclo[3.2.1]octanes, see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
-
-
-
-
64
-
-
0038294333
-
-
For recent approaches, see, for example: b
-
For recent approaches, see, for example: (b) Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821.
-
(2003)
Synlett
, pp. 821
-
-
Kim, J.N.1
Kim, J.M.2
Lee, K.Y.3
-
65
-
-
0028890131
-
-
(c) Ghera, E.; Ramesh, N. G.; Laxer, A.; Hassner, A. Tetrahedron Lett. 1995, 36, 1333.
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 1333
-
-
Ghera, E.1
Ramesh, N.G.2
Laxer, A.3
Hassner, A.4
-
66
-
-
34247875085
-
-
(d) Nicolaou, K. C.; Carenzi, G. E. A.; Jeso, V. Angew. Chem., Int. Ed. 2005, 44, 389.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 389
-
-
Nicolaou, K.C.1
Carenzi, G.E.A.2
Jeso, V.3
-
67
-
-
27544474635
-
-
Hamashima, Y.; Hotta, D.; Umebayashi, N.; Tsuchiya, Y.; Suzuki, T.; Sodeoka, M. Adv. Synth. Catal. 2005, 347, 1576. See also ref 9b.
-
(e) Hamashima, Y.; Hotta, D.; Umebayashi, N.; Tsuchiya, Y.; Suzuki, T.; Sodeoka, M. Adv. Synth. Catal. 2005, 347, 1576. See also ref 9b.
-
-
-
-
69
-
-
85122201594
-
-
For a comprehensive review on the use of cinchona alkaloids in asymmetric synthesis, see
-
For a comprehensive review on the use of cinchona alkaloids in asymmetric synthesis, see: Kacprzak, K.; Gawronski, J. Synthesis 2001, 961.
-
(2001)
Synthesis
, pp. 961
-
-
Kacprzak, K.1
Gawronski, J.2
-
70
-
-
26044441701
-
-
See, e.g, a
-
See, e.g.: (a) Ramachandran, P. V.; Madhi, S.; Bland-Berry, L.; Reddy, M. V. R.; O'Donnell, M. J. J. Am. Chem. Soc. 2005, 127, 13450.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 13450
-
-
Ramachandran, P.V.1
Madhi, S.2
Bland-Berry, L.3
Reddy, M.V.R.4
O'Donnell, M.J.5
-
72
-
-
0035902407
-
-
(c) O'Donnell, M. J.; Delgado, F.; Domínguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 821
-
-
O'Donnell, M.J.1
Delgado, F.2
Domínguez, E.3
de Blas, J.4
Scott, W.L.5
-
73
-
-
0032560703
-
-
(d) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 5347
-
-
Corey, E.J.1
Noe, M.C.2
Xu, F.3
-
74
-
-
0033553450
-
-
(e) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 3843
-
-
Horikawa, M.1
Busch-Petersen, J.2
Corey, E.J.3
-
75
-
-
34247897587
-
-
It should be noted that 6 and 6′ are less effective catalysts compared to 8 and 8′, giving the catalytic product in very low yield. This observation could be justified considering the bulkiness of the adamantoyl group, which might prevent an efficient interaction between the sterically demanding enolate derived from 2 and the quaternary nitrogen. In fact, in the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen, compared to the same counterion in catalyst 8′, presumably due to the steric effects exerted by the adamantoyl group. For a discussion see ref 12h
-
It should be noted that 6 and 6′ are less effective catalysts compared to 8 and 8′, giving the catalytic product in very low yield. This observation could be justified considering the bulkiness of the adamantoyl group, which might prevent an efficient interaction between the sterically demanding enolate derived from 2 and the quaternary nitrogen. In fact, in the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen, compared to the same counterion in catalyst 8′, presumably due to the steric effects exerted by the adamantoyl group. For a discussion see ref 12h.
-
-
-
-
76
-
-
34247857982
-
-
In the case of 5a and 5c, a small amount <10, of the corresponding α,β-unsaturated compounds was detected in the crude mixture, when 50% KOH was used as the base, which could be separated by chromatography from the major γ,δ-unsaturated compounds in both cases
-
In the case of 5a and 5c, a small amount (<10%) of the corresponding α,β-unsaturated compounds was detected in the crude mixture, when 50% KOH was used as the base, which could be separated by chromatography from the major γ,δ-unsaturated compounds in both cases.
-
-
-
-
77
-
-
0347625829
-
-
See, e.g, a
-
See, e.g.: (a) Stapon, A.; Li, R.; Townsend, C. A. J. Am. Chem. Soc. 2003, 125, 15746.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 15746
-
-
Stapon, A.1
Li, R.2
Townsend, C.A.3
-
78
-
-
0037467856
-
-
(b) Bycroft, B. W.; Chhabra, S. R.; Kellam, B.; Smith, P. Tetrahedron Lett. 2003, 44, 973.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 973
-
-
Bycroft, B.W.1
Chhabra, S.R.2
Kellam, B.3
Smith, P.4
-
80
-
-
0032966624
-
-
Bradley, J. S.; Garau, J.; Lode, H.; Rolston, K. V. I.; Wilson, S. E.; Quinn, J. P. Int. J. Antimicrob. Agents 1999, 11, 93.
-
(1999)
Int. J. Antimicrob. Agents
, vol.11
, pp. 93
-
-
Bradley, J.S.1
Garau, J.2
Lode, H.3
Rolston, K.V.I.4
Wilson, S.E.5
Quinn, J.P.6
-
81
-
-
0029843696
-
-
See, e.g, a
-
See, e.g.: (a) Campbell, J. A.; Rapoport, H. J. Org. Chem. 1996, 61, 6313.
-
(1996)
J. Org. Chem
, vol.61
, pp. 6313
-
-
Campbell, J.A.1
Rapoport, H.2
-
82
-
-
0343081412
-
-
(b) Mulzer, J.; Schülzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289.
-
(2000)
Tetrahedron
, vol.56
, pp. 4289
-
-
Mulzer, J.1
Schülzchen, F.2
Bats, J.-W.3
|