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42
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0034600250
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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J. Am. Chem. Soc.
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Ahrendt, K.A.1
Borths, C.J.2
MacMillan, D.W.C.3
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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J. Am. Chem. Soc.
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-
Northrup, A.B.1
MacMillan, D.W.C.2
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0041525915
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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Angew. Chem.
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Juhl, K.1
Jørgensen, K.A.2
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45
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0344835672
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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Angew. Chem. Int. Ed.
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-
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46
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0034638388
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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J. Am. Chem. Soc.
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Jen, W.S.1
Wiener, J.J.M.2
MacMillan, D.W.C.3
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47
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0034807741
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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J. Am. Chem. Soc.
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Paras, N.A.1
MacMillan, D.W.C.2
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48
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0037138701
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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J. Am. Chem. Soc.
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-
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Austin, J.F.1
MacMillan, D.W.C.2
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49
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0037055106
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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MacMillan, D.W.C.2
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For other notable examples of enantioselective organocatalytic reactions, see Diels-Alder reaction: a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243; b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458; hetero-Diels-Alder reaction: c) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536; Angew. Chem. Int. Ed. 2003, 42, 1498; nitrone cycloaddition: d) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874; pyrrole substitution: e) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370; indole substitution: f) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172; aniline substitution: g) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894; Baylis-Hillman reaction: h) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
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PMP = para-methoxyphenyl.
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75
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0042527833
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note
-
DMSO cannot be used at -20°C because it solidifies.
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76
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0042026995
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note
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2 using SHELXL97). CCDC-212084 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
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78
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0042527832
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note
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-1, retention times: 74.6 min (minor) and 80.4 min (major).
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