-
1
-
-
33745412436
-
-
For reviews, see
-
For reviews, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 725
-
-
Regitz, M.1
-
2
-
-
0002138516
-
-
(b) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
-
(2000)
Chem. Rev.
, vol.100
, pp. 39
-
-
Bourissou, D.1
Guerret, O.2
Gabbai, F.P.3
Bertrand, G.4
-
4
-
-
4143051292
-
-
For reviews, see
-
For reviews, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 534
-
-
Enders, D.1
Balensiefer, T.2
-
6
-
-
0042628455
-
-
(c) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
-
(2002)
Chem. Eur. J.
, vol.8
, pp. 5288
-
-
Pohl, M.1
Lingen, B.2
Müller, M.3
-
7
-
-
6044274718
-
-
(d) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
-
(2004)
Angew. Chem. Int. Ed.
, vol.43
, pp. 5130
-
-
Nair, V.1
Bindu, S.2
Sreekumar, V.3
-
12
-
-
0001537080
-
-
For reviews, see
-
For reviews, see: (a) Albright, J. D. Tetrahedron 1983, 39, 3207.
-
(1983)
Tetrahedron
, vol.39
, pp. 3207
-
-
Albright, J.D.1
-
14
-
-
0038375618
-
-
For examples of the benzoin reaction that are not referenced later in the text, see
-
For examples of the benzoin reaction that are not referenced later in the text, see: (a) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 8432
-
-
Hachisu, Y.1
Bode, J.W.2
Suzuki, K.3
-
15
-
-
33745716505
-
-
For examples of the benzoin reaction with acylsilanes, see
-
(b) For examples of the benzoin reaction with acylsilanes, see: Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 1463
-
-
Enders, D.1
Niemeier, O.2
Balensiefer, T.3
-
17
-
-
1642295713
-
-
(d) Linghu, X.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3070
-
-
Linghu, X.1
Potnick, J.R.2
Johnson, J.S.3
-
18
-
-
0001070365
-
-
Paquette, L. A., Ed.; Wiley & Sons: New York
-
Stetter, H.; Kuhlmann, H. In Organic Reactions, Vol.40; Paquette, L. A., Ed.; Wiley & Sons: New York, 1991, 407.
-
(1991)
Organic Reactions
, vol.40
, pp. 407
-
-
Stetter, H.1
Kuhlmann, H.2
-
19
-
-
0011928573
-
Noncatalytic Additions to α,β-Unsaturated Carbonyl Compounds
-
Morrison, J. D., Ed.; Academic Press: New York
-
(a) Tomioka, K.; Koga, K. Noncatalytic Additions to α,β- Unsaturated Carbonyl Compounds, In Asymmetric Synthesis, Vol.2; Morrison, J. D., Ed.; Academic Press: New York, 1983, 201.
-
(1983)
Asymmetric Synthesis
, vol.2
, pp. 201
-
-
Tomioka, K.1
Koga, K.2
-
23
-
-
3142640259
-
-
For the mechanism of the thiamine-catalyzed benzoin reaction, see
-
For the mechanism of the thiamine-catalyzed benzoin reaction, see: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
-
(1958)
J. Am. Chem. Soc.
, vol.80
, pp. 3719
-
-
Breslow, R.1
-
26
-
-
84977252019
-
-
Wöhler, F.; Liebig, J. Ann. Pharm. (Lemgo, Ger.) 1832, 3, 249.
-
(1832)
Ann. Pharm. (Lemgo, Ger.)
, vol.3
, pp. 249
-
-
Wöhler, F.1
Liebig, J.2
-
27
-
-
0000976736
-
-
Ugai, T.; Dokawa, T.; Tsubokawa, S. J. Pharm. Soc. Jpn. 1943, 63, 296.
-
(1943)
J. Pharm. Soc. Jpn.
, vol.63
, pp. 296
-
-
Ugai, T.1
Dokawa, T.2
Tsubokawa, S.3
-
28
-
-
0141553983
-
-
Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5289.
-
(2002)
Chem. Eur. J.
, vol.8
, pp. 5289
-
-
Pohl, M.1
Lingen, B.2
Müller, M.3
-
31
-
-
0000121695
-
-
(a) Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. Soc. Jpn. 1980, 53, 478.
-
(1980)
Bull. Chem. Soc. Jpn.
, vol.53
, pp. 478
-
-
Tagaki, W.1
Tamura, Y.2
Yano, Y.3
-
32
-
-
0027441447
-
-
(b) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 521
-
-
Martí, J.1
Castells, J.2
López-Calahorra, F.3
-
33
-
-
85047673665
-
-
(c) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 4817
-
-
Yamashita, K.1
Sasaki, S.-I.2
Osaki, T.3
Nango, M.4
Tsuda, K.5
-
34
-
-
84990164343
-
-
Igau, A.; Grutzmacher, H.; Baceiredo, A.; Trinquier, G.; Betrand, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 621.
-
(1989)
Angew. Chem., Int. Ed. Engl.
, vol.28
, pp. 621
-
-
Igau, A.1
Grutzmacher, H.2
Baceiredo, A.3
Trinquier, G.4
Betrand, G.5
-
35
-
-
0001286592
-
-
Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 361
-
-
Arduengo III, A.J.1
Harlow, R.L.2
Kline, M.3
-
36
-
-
0000430035
-
-
Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217.
-
(1996)
Helv. Chim. Acta
, vol.79
, pp. 1217
-
-
Enders, D.1
Breuer, K.2
Teles, J.H.3
-
42
-
-
0037120881
-
-
Dünkelmann, P.; Kolter-Jung, D.; Nitsche, A.; Demir, A. S.; Siegert, P.; Lingen, B.; Baumann, M.; Pohl, M.; Müller, M. J. Am. Chem. Soc. 2002, 124, 12084.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 12084
-
-
Dünkelmann, P.1
Kolter-Jung, D.2
Nitsche, A.3
Demir, A.S.4
Siegert, P.5
Lingen, B.6
Baumann, M.7
Pohl, M.8
Müller, M.9
-
43
-
-
33745716505
-
-
(a) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 1463
-
-
Enders, D.1
Niemeier, O.2
Balensiefer, T.3
-
45
-
-
33745722719
-
-
Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 3492
-
-
Takikawa, H.1
Hachisu, Y.2
Bode, J.W.3
Suzuki, K.4
-
47
-
-
1642295713
-
-
Linghu, X.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3070
-
-
Linghu, X.1
Potnick, J.R.2
Johnson, J.S.3
-
48
-
-
22144480983
-
-
Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 5725
-
-
Kerr, M.S.1
Read De Alaniz, J.2
Rovis, T.3
-
53
-
-
0030822243
-
-
(b) Smrcina, M.; Majer, P.; Majerová, E.; Guerassina, T. A.; Eissenstat, M. A. Tetrahedron 1997, 53, 12867.
-
(1997)
Tetrahedron
, vol.53
, pp. 12867
-
-
Smrcina, M.1
Majer, P.2
Majerová, E.3
Guerassina, T.A.4
Eissenstat, M.A.5
-
54
-
-
0000011522
-
Addition of Acyl Carbanion Equivalents to Carbonyl Groups and Enones
-
Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin
-
(a) Enders, D.; Breuer, K. Addition of Acyl Carbanion Equivalents to Carbonyl Groups and Enones, In Comprehensive Asymmetric Catalysis I-III, Vol.3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999, 1093.
-
(1999)
Comprehensive Asymmetric Catalysis I-III
, vol.3
, pp. 1093
-
-
Enders, D.1
Breuer, K.2
-
56
-
-
33644652260
-
-
and references cited therein
-
Nahm, M. R.; Potnick, J. R.; White, P. S.; Johnson, J. S. J. Am. Chem. Soc. 2006, 128, 2751; and references cited therein.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 2751
-
-
Nahm, M.R.1
Potnick, J.R.2
White, P.S.3
Johnson, J.S.4
-
57
-
-
1542375011
-
-
For related examples of acylsilanes in the Stetter reaction, see
-
For related examples of acylsilanes in the Stetter reaction, see: (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 2314
-
-
Mattson, A.E.1
Bharadwaj, A.R.2
Scheidt, K.A.3
-
59
-
-
33646146207
-
-
Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4932.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 4932
-
-
Mattson, A.E.1
Zuhl, A.M.2
Reynolds, T.E.3
Scheidt, K.A.4
-
61
-
-
0018422536
-
-
For a seminal example of an intramolecular Stetter reaction, see
-
(b) For a seminal example of an intramolecular Stetter reaction, see: Trost, B. M.; Shuey, C. D.; DiNinno, F.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1284.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 1284
-
-
Trost, B.M.1
Shuey, C.D.2
DiNinno, F.3
McElvain, S.S.4
-
62
-
-
0001710837
-
-
Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
-
(1996)
Helv. Chim. Acta
, vol.79
, pp. 1899
-
-
Enders, D.1
Breuer, K.2
Runsink, J.3
Teles, J.H.4
-
64
-
-
12744273171
-
-
Mennen, S. M.; Blank, J. T.; Tran-Dubé, M. B.; Imbriglio, J. E.; Miller, S. J. Chem. Commun. 2005, 195.
-
(2005)
Chem. Commun.
, pp. 195
-
-
Mennen, S.M.1
Blank, J.T.2
Tran-Dubé, M.B.3
Imbriglio, J.E.4
Miller, S.J.5
-
66
-
-
0037019628
-
-
(a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10298
-
-
Kerr, M.S.1
Read De Alaniz, J.2
Rovis, T.3
-
67
-
-
41849101072
-
-
(b) Read de Alaniz, J.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 2033
-
-
Read De Alaniz, J.1
Kerr, M.S.2
Moore, J.L.3
Rovis, T.4
-
68
-
-
67649325189
-
-
note
-
Investigation of the enantioselectivity as a function of conversion revealed that 80 is formed in 80% ee at 10% conversion, with rapid erosion to 50% ee at 30% conversion.
-
-
-
-
69
-
-
67649357436
-
-
note
-
Similar observations have been noted by Miller and co-workers; see reference 40.
-
-
-
-
71
-
-
0000648351
-
-
(a) Minowa, N.; Hirayama, M.; Fukatsu, S. Tetrahedron Lett. 1984, 25, 1147.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 1147
-
-
Minowa, N.1
Hirayama, M.2
Fukatsu, S.3
-
72
-
-
0028303642
-
-
(b) Ruiz, M.; Ojea, V.; Shapiro, G.; Weber, H. P.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 4551.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 4551
-
-
Ruiz, M.1
Ojea, V.2
Shapiro, G.3
Weber, H.P.4
Pombo-Villar, E.5
-
73
-
-
0033572920
-
-
(c) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11591
-
-
Hayashi, T.1
Senda, T.2
Takaya, Y.3
Ogasawara, M.4
-
74
-
-
33750492925
-
-
(d) Fernández, M.; Diaz, A.; Guillin, J. J.; Blanco, O.; Ruiz, M.; Ojea, V. J. Org. Chem. 2006, 71, 6958.
-
(2006)
J. Org. Chem.
, vol.71
, pp. 6958
-
-
Fernández, M.1
Diaz, A.2
Guillin, J.J.3
Blanco, O.4
Ruiz, M.5
Ojea, V.6
-
75
-
-
34250210543
-
-
(e) Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6996.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 6996
-
-
Kondoh, A.1
Yorimitsu, H.2
Oshima, K.3
-
76
-
-
49749142458
-
-
(f) Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem. Int. Ed. 2008, 47, 3410.
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 3410
-
-
Nishida, G.1
Noguchi, K.2
Hirano, M.3
Tanaka, K.4
-
77
-
-
34848850097
-
-
(g) Sulzer-Mossé, S.; Tissot, M.; Alexakis, A. Org. Lett. 2007, 9, 3749.
-
(2007)
Org. Lett.
, vol.9
, pp. 3749
-
-
Sulzer-Mossé, S.1
Tissot, M.2
Alexakis, A.3
-
78
-
-
38049125106
-
-
(h) Capuzzi, M.; Perdicchia, D.; Jørgensen, K. A. Chem. Eur. J. 2008, 14, 128.
-
(2008)
Chem. Eur. J.
, vol.14
, pp. 128
-
-
Capuzzi, M.1
Perdicchia, D.2
Jørgensen, K.A.3
-
85
-
-
0018422536
-
-
Trost, B. M.; Shuey, C. D.; DiNinno, F. Jr.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1284.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 1284
-
-
Trost, B.M.1
Shuey, C.D.2
DiNinno Jr., F.3
McElvain, S.S.4
-
86
-
-
33750440190
-
-
Moore, J. L.; Kerr, M. S.; Rovis, T. Tetrahedron 2006, 62, 11477.
-
(2006)
Tetrahedron
, vol.62
, pp. 11477
-
-
Moore, J.L.1
Kerr, M.S.2
Rovis, T.3
-
88
-
-
0001302486
-
-
For examples of intramolecular proton transfer, see
-
For examples of intramolecular proton transfer, see: (a) Zimmerman, H. E. Acc. Chem. Res. 1987, 20, 263.
-
(1987)
Acc. Chem. Res.
, vol.20
, pp. 263
-
-
Zimmerman, H.E.1
-
89
-
-
0012144938
-
-
and references cited therein
-
(b) Zimmerman, H. E.; Wang, P. Org. Lett. 2002, 4, 2593; and references cited therein.
-
(2002)
Org. Lett.
, vol.4
, pp. 2593
-
-
Zimmerman, H.E.1
Wang, P.2
-
91
-
-
0033599528
-
-
It is also possible that the α-hydroxy-α-azolium anion adds to the Michael acceptor in concerted fashion, analogous to the reverse-Cope elimination mechanism seen with hydroxylamine additions; see
-
It is also possible that the α-hydroxy-α-azolium anion adds to the Michael acceptor in concerted fashion, analogous to the reverse-Cope elimination mechanism seen with hydroxylamine additions; see: (a) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 2456
-
-
Niu, D.1
Zhao, K.2
-
93
-
-
0141732263
-
-
(c) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 11796
-
-
Sibi, M.P.1
Prabagaran, N.2
Ghorpade, S.G.3
Jasperse, C.P.4
-
97
-
-
67649348741
-
-
51
-
51..
-
-
-
-
98
-
-
0026504865
-
-
(c) Baumann, K. L.; Butler, D. E.; Deering, C. F.; Mennen, K. E.; Millar, A.; Nanninga, T. N.; Palmer, C. W.; Roth, B. D. Tetrahedron Lett. 1992, 33, 2283.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 2283
-
-
Baumann, K.L.1
Butler, D.E.2
Deering, C.F.3
Mennen, K.E.4
Millar, A.5
Nanninga, T.N.6
Palmer, C.W.7
Roth, B.D.8
-
101
-
-
7044254973
-
-
(f) Anjaiah, S.; Chandrasekhar, S.; Gree, R. Adv. Synth. Catal. 2004, 346, 1329.
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 1329
-
-
Anjaiah, S.1
Chandrasekhar, S.2
Gree, R.3
-
104
-
-
54849432201
-
-
Liu, Q.; Perreault, S.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14066.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 14066
-
-
Liu, Q.1
Perreault, S.2
Rovis, T.3
|