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b) M. R. Boyd, Y. F. Hallock, J. H. Cardellina II, K. P. Manfredi, J. W. Blunt, J. B. McMahon, R. W. Buckheit, G. Bringmann, M. Schaffer, G. M. Cragg, D. W. Thomas, J. G. Jato, J. Med. Chem. 1994, 37, 1740-1745;
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15644384271
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Y. F. Hallock, K. P. Manfredi, J. W. Blunt, J. H. Cardellina II, M. Schäffer, K. P. Gulden, G. Bringmann, A. Y. Lee, J. Clardy, G. François, M. R. Boyd, J. Org. Chem. 1994, 59, 6349-6355.
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Gulden, K.P.6
Bringmann, G.7
Lee, A.Y.8
Clardy, J.9
François, G.10
Boyd, M.R.11
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6
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0001537132
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a) G. Bringmann, R. Götz, P. A. Keller, R. Walter, P. Henschel, M. Schäffer, M. Stäblein, T. R. Kelly, M. R. Boyd, Heterocycles 1994, 39, 503-508;
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Walter, R.4
Henschel, P.5
Schäffer, M.6
Stäblein, M.7
Kelly, T.R.8
Boyd, M.R.9
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0029874643
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b) P. D. Hobbs, V. Upender, J. Liu, D. J. Pollart, D. W. Thomas, M. Dawson, Chem. Commun. 1996, 923-924; P. D. Hobbs, V. Upender, M. I. Dawson, Synlett 1997, 965-967;
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Dawson, M.6
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0001321058
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b) P. D. Hobbs, V. Upender, J. Liu, D. J. Pollart, D. W. Thomas, M. Dawson, Chem. Commun. 1996, 923-924; P. D. Hobbs, V. Upender, M. I. Dawson, Synlett 1997, 965-967;
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c) T. R. Hoye, M. Chen, Tetrahedron Lett. 1996, 37, 3099-3100; T. R. Hoye, M.Chen, L. Mi, O. P. Priest, Tetrahedron Lett. 1994, 35, 8747-8750;
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0028020526
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c) T. R. Hoye, M. Chen, Tetrahedron Lett. 1996, 37, 3099-3100; T. R. Hoye, M.Chen, L. Mi, O. P. Priest, Tetrahedron Lett. 1994, 35, 8747-8750;
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Hoye, T.R.1
Chen, M.2
Mi, L.3
Priest, O.P.4
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12
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0032917881
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a) G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558; G. Bringmann, M. Ochse, Synlett 1998, 1294-1296; G. Bringmann, R. Gotz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, I. Tellitu, V. Bhaskar, T. R. Kelly, J. Org. Chem. 1998, 63, 1090- 1097; G. Bringmann, D. Vitt, J. Org. Chem. 1995, 60, 7674-7681;
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Bringmann, G.1
Breuning, M.2
Tasler, S.3
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13
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26844576958
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a) G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558; G. Bringmann, M. Ochse, Synlett 1998, 1294-1296; G. Bringmann, R. Gotz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, I. Tellitu, V. Bhaskar, T. R. Kelly, J. Org. Chem. 1998, 63, 1090- 1097; G. Bringmann, D. Vitt, J. Org. Chem. 1995, 60, 7674-7681;
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Synlett
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Bringmann, G.1
Ochse, M.2
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14
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7144259775
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a) G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558; G. Bringmann, M. Ochse, Synlett 1998, 1294-1296; G. Bringmann, R. Gotz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, I. Tellitu, V. Bhaskar, T. R. Kelly, J. Org. Chem. 1998, 63, 1090-1097; G. Bringmann, D. Vitt, J. Org. Chem. 1995, 60, 7674-7681;
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Bringmann, G.1
Gotz, R.2
Keller, P.A.3
Walter, R.4
Boyd, M.R.5
Lang, F.6
Garcia, A.7
Walsh, J.J.8
Tellitu, I.9
Bhaskar, V.10
Kelly, T.R.11
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15
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0001179537
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a) G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558; G. Bringmann, M. Ochse, Synlett 1998, 1294-1296; G. Bringmann, R. Gotz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, I. Tellitu, V. Bhaskar, T. R. Kelly, J. Org. Chem. 1998, 63, 1090- 1097; G. Bringmann, D. Vitt, J. Org. Chem. 1995, 60, 7674-7681;
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Bringmann, G.1
Vitt, D.2
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17
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0345628806
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c) A. V Rama Rao, M. K. Gurjar, V. Ramana, A. K. Chheda, Heterocycles 1996, 43, 1-6. Other representative alternative routes to atropselective biaryl couplings include T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101-9102; A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769.
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Rama Rao, A.V.1
Gurjar, M.K.2
Ramana, V.3
Chheda, A.K.4
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18
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0001578739
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-
c) A. V Rama Rao, M. K. Gurjar, V. Ramana, A. K. Chheda, Heterocycles 1996, 43, 1-6. Other representative alternative routes to atropselective biaryl couplings include T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101-9102; A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769.
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Hayashi, T.1
Niizuma, S.2
Kamikawa, T.3
Suzuki, N.4
Uozumi, Y.5
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19
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0033620428
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c) A. V Rama Rao, M. K. Gurjar, V. Ramana, A. K. Chheda, Heterocycles 1996, 43, 1-6. Other representative alternative routes to atropselective biaryl couplings include T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101-9102; A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769.
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Degnan, A.P.1
Meyers, A.I.2
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20
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84988122964
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-
For a related route to the required 1.3-dimethylated tetrahydroisoquinolines, see G. Bringmann, R. Weirich, H. Reuscher, J. R. Jansen, L. Kinzinger, T. Ortmann, Liebigs Ann. Chem. 1993, 877-888.
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Liebigs Ann. Chem.
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Bringmann, G.1
Weirich, R.2
Reuscher, H.3
Jansen, J.R.4
Kinzinger, L.5
Ortmann, T.6
-
21
-
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85077634689
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O. Mitsunobu, Synthesis 1981, 1-28; D. Hughes, Org. React. (N.Y.) 1992, 42, 335-395.
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(1981)
Synthesis
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Mitsunobu, O.1
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22
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85077634689
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O. Mitsunobu, Synthesis 1981, 1-28; D. Hughes, Org. React. (N.Y.) 1992, 42, 335-395.
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Org. React. (N.Y.)
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Hughes, D.1
-
23
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84920345006
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-
note
-
Reactions run at 85°C generally gave good results, but heating to >90°C afforded low yields. See also ref. [5].
-
-
-
-
24
-
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84920360427
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-
Solubilized LAH gave lower selectivities for the trans isomer
-
Solubilized LAH gave lower selectivities for the trans isomer.
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-
-
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25
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0028020526
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T. R. Hoye, M. Chen, L. Mi, O. P. Priest, Tetrahedron Lett. 1994, 35, 8747-8750.
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 8747-8750
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Hoye, T.R.1
Chen, M.2
Mi, L.3
Priest, O.P.4
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28
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0030857708
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C. Coudret, V. Manzenc, Tetrahedron Lett. 1997, 38, 5293-5296; F. Liu, E. Negishi, J. Org. Chem. 1997, 62, 8591-8594.
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Coudret, C.1
Manzenc, V.2
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29
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0004789384
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C. Coudret, V. Manzenc, Tetrahedron Lett. 1997, 38, 5293-5296; F. Liu, E. Negishi, J. Org. Chem. 1997, 62, 8591-8594.
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J. Org. Chem.
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Liu, F.1
Negishi, E.2
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30
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0031568727
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K. Bouruneau, A. C. Gaumont, J. M. Dennis, J. Organomet. Chem. 1997, 529, 205-213.
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J. Organomet. Chem.
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Bouruneau, K.1
Gaumont, A.C.2
Dennis, J.M.3
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31
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0003719460
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a) B. Breit, Liebigs Ann. Chem. 1997, 1841-1851; B. Breit, Angew. Chem. 1998, 110, 535-538; Angew. Chem. Int. Ed. 1998, 37, 525-527;
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Liebigs Ann. Chem.
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Breit, B.1
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32
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0001565533
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a) B. Breit, Liebigs Ann. Chem. 1997, 1841-1851; B. Breit, Angew. Chem. 1998, 110, 535-538; Angew. Chem. Int. Ed. 1998, 37, 525-527;
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Angew. Chem.
, vol.110
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-
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Breit, B.1
-
33
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0032473439
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a) B. Breit, Liebigs Ann. Chem. 1997, 1841-1851; B. Breit, Angew. Chem. 1998, 110, 535-538; Angew. Chem. Int. Ed. 1998, 37, 525-527;
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Angew. Chem. Int. Ed.
, vol.37
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-
-
-
34
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0009127351
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b) B. M. Trost, C. Marschner, Bull. Soc. Chim. Fr. 1997, 134, 263-274; B. M. Trost, D. L. van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343; for examples of related directing effects by an internal phosphane, see C. N. Farthing, P. Kocovsky, J. Am. Chem. Soc. 1998, 120, 6661-6672; M. T. Didiuk, J. P. Morken, A. H. Hoveyda, Tetrahedron, 1998, 54, 1117-1130, and references therein.
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Bull. Soc. Chim. Fr.
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Trost, B.M.1
Marschner, C.2
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35
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1642324310
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-
b) B. M. Trost, C. Marschner, Bull. Soc. Chim. Fr. 1997, 134, 263-274; B. M. Trost, D. L. van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343; for examples of related directing effects by an internal phosphane, see C. N. Farthing, P. Kocovsky, J. Am. Chem. Soc. 1998, 120, 6661-6672; M. T. Didiuk, J. P. Morken, A. H. Hoveyda, Tetrahedron, 1998, 54, 1117-1130, and references therein.
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J. Am. Chem. Soc.
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Trost, B.M.1
Van Vranken, D.L.2
Bingel, C.3
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36
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2642670293
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b) B. M. Trost, C. Marschner, Bull. Soc. Chim. Fr. 1997, 134, 263-274; B. M. Trost, D. L. van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343; for examples of related directing effects by an internal phosphane, see C. N. Farthing, P. Kocovsky, J. Am. Chem. Soc. 1998, 120, 6661-6672; M. T. Didiuk, J. P. Morken, A. H. Hoveyda, Tetrahedron, 1998, 54, 1117-1130, and references therein.
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J. Am. Chem. Soc.
, vol.120
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-
Farthing, C.N.1
Kocovsky, P.2
-
37
-
-
0032510190
-
-
and references therein
-
b) B. M. Trost, C. Marschner, Bull. Soc. Chim. Fr. 1997, 134, 263-274; B. M. Trost, D. L. van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343; for examples of related directing effects by an internal phosphane, see C. N. Farthing, P. Kocovsky, J. Am. Chem. Soc. 1998, 120, 6661-6672; M. T. Didiuk, J. P. Morken, A. H. Hoveyda, Tetrahedron, 1998, 54, 1117-1130, and references therein.
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(1998)
Tetrahedron
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-
-
Didiuk, M.T.1
Morken, J.P.2
Hoveyda, A.H.3
-
38
-
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84920360731
-
-
note
-
[1d] it is appreciated that structural changes with such tetrahydroisoquinolines can alter the observed CD spectra, thereby leading to erroneous assignments. In the case of derivatives 16, it is apparent that alterations at the C-3 methyl group do not impact, let alone overshadow, the significant bias imposed in each by the axially chiral, nonracemic, biaryl nuclei.
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