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For a general review on chiral diamines: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
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Lucet, D.1
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0032538362
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For a general review on chiral diamines: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
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Bennani, Y.L.1
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0029817010
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Selected examples of asymmetric stoichiometric transformations: a) E. J. Corey, S. Sarshar, M. D. Azimioara, R. C. Newbold, M. C. Noe, J. Am. Chem. Soc. 1996, 118, 7851;
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Murata, K.1
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e) M. Nakajima, I. Miyoshi, K. Kanayama, S.-i. Hashimoto, M. Noji, K. Koga, J. Org. Chem. 1999, 64, 2264;
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Nakajima, M.1
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f) L. Cavallo, M. E. Cucciolito, A. De Martino, F. Giordano, I. Orabona, A. Vitagliano, Chem. Eur. J. 2000, 6, 1127.
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11
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0035977261
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Selected examples of asymmetric catalytic transformations: a) R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7931;
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Noyori, R.1
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Magnus, A.1
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d) K. Kubota, J. L. Leighton, Angew. Chem. 2003, 115, 976; Angew. Chem. Int. Ed. 2003, 42, 946;
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Kubota, K.1
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d) K. Kubota, J. L. Leighton, Angew. Chem. 2003, 115, 976; Angew. Chem. Int. Ed. 2003, 42, 946;
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18
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37649026044
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For outstanding examples of highly efficient asymmetric molecular catalysts containing chiral 1,2-diamines: a) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40; Angew. Chem. Int. Ed. 2001, 40, 40;
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Noyori, R.1
Ohkuma, T.2
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19
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37649026044
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For outstanding examples of highly efficient asymmetric molecular catalysts containing chiral 1,2-diamines: a) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40; Angew. Chem. Int. Ed. 2001, 40, 40;
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Angew. Chem. Int. Ed.
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20
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b) T. Ohkuma, M. Koizumi, K. Muñiz, G. Hilt, C. Kabuto, R. Noyori, J. Am. Chem. Soc. 2002, 124, 6508.
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Ohkuma, T.1
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a) J. Gawronski, K. Gawronska, J. Grajewski, K. Kacprzak, U. Rychleska, Chem. Commun. 2002, 582;
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Chem. Commun.
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Gawronski, J.1
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d) K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem. 1996, 108, 2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1949.
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Hanabusa, K.1
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0029989364
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0036456907
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For an excellent schematic overview on synthetic routes: D. Enders, M. Meiers, Synthesis 2002, 2542.
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Synthesis
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Enders, D.1
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Standard resolution of 1,2-diamino cyclohexane: J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Noie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939.
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0001539022
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Selected examples: a) N. Taniguchi, T. Hata, M. Uemura, Angew. Chem. 1999, 111, 1311; Angew. Chem. Int. Ed. 1999, 38, 1232;
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Taniguchi, N.1
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Selected examples: a) N. Taniguchi, T. Hata, M. Uemura, Angew. Chem. 1999, 111, 1311; Angew. Chem. Int. Ed. 1999, 38, 1232;
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Larsen, A.O.1
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Campos, P.J.1
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Enders, D.1
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34
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Selected examples: a) D. Enders, M. Meiers, Angew. Chem. 1996, 108, 2391; Angew. Chem. Int. Ed. Engl. 1996, 35, 2261;
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Angew. Chem. Int. Ed. Engl.
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b) B. Westermann, Angew. Chem. 2003, 115, 161; Angew. Chem. Int. Ed. 2003, 42, 151;
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Westermann, B.1
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38
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0343421593
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d) A. Alexakis, A. Tomassini, C. Chouillet, S. Roland, P. Mangeney, G. Bernardinelli, Angew. Chem. 2000, 112, 4259; Angew. Chem. Int. Ed. 2000, 39, 4093;
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Alexakis, A.1
Tomassini, A.2
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d) A. Alexakis, A. Tomassini, C. Chouillet, S. Roland, P. Mangeney, G. Bernardinelli, Angew. Chem. 2000, 112, 4259; Angew. Chem. Int. Ed. 2000, 39, 4093;
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40
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0034644584
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e) G. Martinelli, S. Morri, D. Savoia, Tetrahedron 2000, 56, 8367;
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Tetrahedron
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Martinelli, G.1
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Li, Z.1
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related diamine synthesis from racemic aziridinium compounds
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b) J. E. W. Scheuermann, G. Ilyashenko, D. V. Griffiths, M. Watkinson, Tetrahedron: Asymmetry 2002, 13, 269;
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Scheuermann, J.E.W.1
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related diamine synthesis from racemic aziridinium compounds: c) T.-H. Chuang, K. B. Sharpless, Org. Lett. 1999, 1, 1435;
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f) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056; Angew. Chem. Int. Ed. 2001, 40, 2004.
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Kolb, H.C.1
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f) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056; Angew. Chem. Int. Ed. 2001, 40, 2004.
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Lee, S.-G.1
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b) related diamine synthesis via aza-Claisen rearrangement: J. Gonda, A.-C. Helland, B. Ernst, D. Bellus, Synthesis 1993, 729.
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0347266525
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c) Note, however, that all products from these reactions are achiral.
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Li, G.1
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79
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0035915127
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a) G. Li, H.-X. Wei, S. H. Kim, M. Carducci, Angew. Chem. 2001, 113, 4407; Angew. Chem. Int. Ed. 2001, 40, 4277;
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80
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0037067329
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b) H.-X. Wei, S. H. Kim, G. Li, J. Org. Chem. 2002, 67, 4777;
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Wei, H.-X.1
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Wie, H.-X.1
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82
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0034605847
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For an uncatalysed version: G. Li, S. H. Kim, H.-X. Wie, Tetrahedron Lett. 2000, 41, 8699.
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Li, G.1
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0018542252
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0034714168
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b) H. X. Zhang, P. Xia, W. S. Zhou, Tetrahedron: Asymmetry 2000, 11, 3439;
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Zhang, H.X.1
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92
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0347266523
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Criegee, R.1
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94
-
-
0347896830
-
-
note
-
An alternative interpretation consists of reversible or stepwise addition of 2 to the (Z)-configured olefin. Thus, an isomerization of the olefin geometry or of the internal C-C bond after addition of the first imino group might also be possible. However, this assumption does not explain the additional isomerisation after isolation of the mixture. The slow reaction rate and the low yield of this transformation made additional investigation rather complicated.
-
-
-
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97
-
-
33749095543
-
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Recent structural determinations: a) A. Lehtonen, J. Jokela, P. G. Edwards, R. Sillanpäa, J. Chem. Soc. Dalton Trans. 1999, 2785;
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J. Chem. Soc. Dalton Trans.
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Lehtonen, A.1
Jokela, J.2
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Sillanpäa, R.4
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98
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0011291716
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b) M. R. Sivik, J. C. Gallucci, L. A. Paquette, J. Org. Chem. 1990, 55, 391;
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Sivik, M.R.1
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102
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0000642622
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b) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345;
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Herrmann, W.A.1
Eder, S.J.2
Scherer, W.3
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103
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33748244629
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b) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345;
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Angew. Chem. Int. Ed. Engl.
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104
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84985704514
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c) W. A. Herrmann, S. J. Eder, W. Scherer, Chem. Ber. 1993, 126, 39;
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Herrmann, W.A.1
Eder, S.J.2
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105
-
-
0347266521
-
-
note
-
d) further structures deposited at CCDC bear the following identification codes: OLATOS, QERCUL, MBAOOS, MTOLOS, OSOTYM, MAYDIZ, ADPYOS10, HOMMAX, HOMMEB and VIGPIK.
-
-
-
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106
-
-
0347266516
-
-
R. M. Pearlstein, B. K. Blackburn, M. W. Davis, K. B. Sharpless, Angew. Chem. 1990, 102, 710; Angew. Chem. Int. Ed. Engl. 1990, 29, 639.
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Pearlstein, R.M.1
Blackburn, B.K.2
Davis, M.W.3
Sharpless, K.B.4
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107
-
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33748233298
-
-
R. M. Pearlstein, B. K. Blackburn, M. W. Davis, K. B. Sharpless, Angew. Chem. 1990, 102, 710; Angew. Chem. Int. Ed. Engl. 1990, 29, 639.
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Angew. Chem. Int. Ed. Engl.
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-
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108
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-
0001077871
-
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Recent structural determinations: a) K. Tomioka, M. Nakajima, Y. Iitaka, K. Koga, Tetrahedron Lett. 1988, 29, 573;
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Tomioka, K.1
Nakajima, M.2
Iitaka, Y.3
Koga, K.4
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109
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0027374787
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b) M. Nakajima, K. Tomioka, Y. Iitaka, K. Koga, Tetrahedron 1993, 49, 10793;
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Nakajima, M.1
Tomioka, K.2
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Koga, K.4
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111
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0032569921
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d) T. J. Donohoe, K. Blades, M. Helliwell, M. J. Waring, N. J. Newcombe, Tetrahedron Lett. 1998, 39, 8755;
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Donohoe, T.J.1
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112
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0037111592
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e) T. J. Donohoe, K. Blades, P. R. Moore, M. J. Waring, J. J. G. Winter, M. Helliwell, N. J. Newcombe, G. Stemp, J. Org. Chem. 2002, 67, 7946.
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Donohoe, T.J.1
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Helliwell, M.6
Newcombe, N.J.7
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114
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37049107242
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b) B. A. Cartwright, W. P. Griffith, M. Schröder, A. C. Skapski, J. Chem. Soc. Chem. Commun. 1978, 853.
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115
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0037032268
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Structural determinations: a) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12934;
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J. Am. Chem. Soc.
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Donohoe, T.J.1
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0005136972
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b) W. P. Griffith, N. T. MaManus, A. C. Skapski, A. J. Nielson, Inorg. Chim. Acta 1985, 103, L5.
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Griffith, W.P.1
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117
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0000675869
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A. E. Rubin, K. B. Sharpless, Angew. Chem. 1997, 109, 2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2637.
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Rubin, A.E.1
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118
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0031573889
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A. E. Rubin, K. B. Sharpless, Angew. Chem. 1997, 109, 2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2637.
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119
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0001305539
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a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455;
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Fokin, V.V.1
Sharpless, K.B.2
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120
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0035903613
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a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455;
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121
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0000451948
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b) P. Dupau, R. Epple, A. A. Thomas, V. V. Fokin, K. B. Sharpless, Adv. Synth. Catal. 2002, 344, 421;
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Adv. Synth. Catal.
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Dupau, P.1
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122
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0037784368
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c) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472;
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Andersson, M.A.1
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123
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0036462501
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c) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472;
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124
-
-
0346005527
-
-
see also ref. [12f]
-
d) see also ref. [12f].
-
-
-
-
125
-
-
0029074988
-
-
and references therein
-
The products obtained thereby are interesting derivatives of α,β-diamino acids that represent biologically interesting compounds. See, for example: Y. Nakamura, M. Hirai, K. Tamotsu, Y. Yonezawa, C.-G. Shin, Bull. Chem. Soc. Jpn. 1995, 68, 1369 and references therein.
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Nakamura, Y.1
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126
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0039641133
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For original work by Sharpless on reaction of 1 with olefins, see: a) K. B. Sharpless, D. W. Patrick, L. K. Truesdale, S. A. Biller, J. Am. Chem. Soc. 1975, 97, 2305;
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33947092269
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b) D. W. Patrick, L. K. Truesdale, S. A. Biller, K. B. Sharpless, J. Org. Chem. 1978, 43, 2628;
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129
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0347896825
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see also footnote [16] in ref. [21]
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d) see also footnote [16] in ref. [21].
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131
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25044434957
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unpublished results, Universität Bonn
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K. Muñiz, unpublished results, Universität Bonn, 2002.
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Muñiz, K.1
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137
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0347266515
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-
note
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A single example of substrate-directed olefin diamination has been described by Barluenga et al. for the mercury-mediated diamination of (R)-limonene, albeit the reaction gave a product mixture.[23b]
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138
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141
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0033597413
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For chiral acrylic amides bearing Oppolzer sultams as chiral auxiliaries in related ruthenium-catalysed dihydroxylation reactions: A. W. M. Lee, W. H. Chan, W. H. Yuen, P. F. Xia, W. Y. Wong, Tetrahedron: Asymmetry 1999, 10, 1421.
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L. Mangatal, M.-T Adeline, D. Guénard, F. Gué ritte-Voegelein, P. Potier, Tetrahedron 1989, 45, 4177.
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a) J. Barluenga, J. M. Montserrat, J. Flórez, S. García-Granda, E. Martín, Angew. Chem. 1994, 106, 1451; Angew. Chem. Int. Ed. Engl. 1994, 33, 1392;
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a) J. Barluenga, J. M. Montserrat, J. Flórez, S. García-Granda, E. Martín, Angew. Chem. 1994, 106, 1451; Angew. Chem. Int. Ed. Engl. 1994, 33, 1392;
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Recently, a related report on transition metal catalysed transamination has appeared: S. E. Eldred, D. A. Stone, S. H. Gellman, S. S. Stahl, J. Am. Chem. Soc. 2003, 125, 3422.
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a) E. N. Jacobsen, I. Marko, M. B. France, J. S. Svendson, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 737;
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Jacobsen, E.N.1
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157
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0001091776
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Review: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
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Berrisford, D.J.1
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158
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33748983103
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Review: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
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0000829650
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For the prime example: a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997. 36, 285;
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For the prime example: a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997. 36, 285;
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C. R. Hauser, B. E. Hudson, B. Abramovitch, J. C. Shivers, Org. Synth. Coll. Vol. III 1955, 142, 144.
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