Ligand-mediated addition of organometallic reagents to azomethine functions

Chemical Communications

Volumn , Issue 9, 1996, Pages 999-1004

  Denmark, Scott E ^a,c,d   Nicaise, Olivier J C ^a,b,e,f  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^c MIT

^d ETH ZURICH   (Switzerland)

^e SORBONNE UNIVERSITÉ   (France)

^f UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002569664     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000999     Document Type: Article

References (75)

1. For a recent monograph on practical methods of stereoselective synthesis, see: M. Nógrádi, Stereoselective Synthesis: A Practical Approach, 2nd Edition, VCH Verlagsgesellschaft mbH, Weinheim, 1995.
2. For a general review on asymmetric synthesis, see: (a) Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1983-1985; 5 vols, (b) Chem. Br., 1989, 25, 3.
3. For a general review on asymmetric synthesis, see: (a) Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1983-1985; 5 vols, (b) Chem. Br., 1989, 25, 3.
4. For references related to the industrial production and applications of optically active materials, see: (a) Chirality in Industry - The Commercial Manufacture and Applications of Optically Active Compounds, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, John Wiley & Sons, Chichester, 1992; (b) J. W. Scott, Top. Stereochem., 1989, 19, 209; (c) G. W. Parshall and W. A. Nugent, CHEMTECH, 1988, 184, 314, 376; (d) H. B. Kagan, Bull. Soc. Chim. Fr., 1988, 846.
5. For references related to the industrial production and applications of optically active materials, see: (a) Chirality in Industry - The Commercial Manufacture and Applications of Optically Active Compounds, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, John Wiley & Sons, Chichester, 1992; (b) J. W. Scott, Top. Stereochem., 1989, 19, 209; (c) G. W. Parshall and W. A. Nugent, CHEMTECH, 1988, 184, 314, 376; (d) H. B. Kagan, Bull. Soc. Chim. Fr., 1988, 846.
6. For references related to the industrial production and applications of optically active materials, see: (a) Chirality in Industry - The Commercial Manufacture and Applications of Optically Active Compounds, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, John Wiley & Sons, Chichester, 1992; (b) J. W. Scott, Top. Stereochem., 1989, 19, 209; (c) G. W. Parshall and W. A. Nugent, CHEMTECH, 1988, 184, 314, 376; (d) H. B. Kagan, Bull. Soc. Chim. Fr., 1988, 846.
7. For references related to the industrial production and applications of optically active materials, see: (a) Chirality in Industry - The Commercial Manufacture and Applications of Optically Active Compounds, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, John Wiley & Sons, Chichester, 1992; (b) J. W. Scott, Top. Stereochem., 1989, 19, 209; (c) G. W. Parshall and W. A. Nugent, CHEMTECH, 1988, 184, 314, 376; (d) H. B. Kagan, Bull. Soc. Chim. Fr., 1988, 846.
8. For reviews on the asymmetric synthesis of amines and amine derivatives via stabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) E. F. Kleinman, in Comprehensive Organic Synthesis; Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.1; (b) G. I. Georg, in Studies in Natural Products Chemistry - C; ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol. 4, p. 431; (c) D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447.
9. For reviews on the asymmetric synthesis of amines and amine derivatives via stabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) E. F. Kleinman, in Comprehensive Organic Synthesis; Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.1; (b) G. I. Georg, in Studies in Natural Products Chemistry - C; ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol. 4, p. 431; (c) D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447.
10. For reviews on the asymmetric synthesis of amines and amine derivatives via stabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) E. F. Kleinman, in Comprehensive Organic Synthesis; Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.1; (b) G. I. Georg, in Studies in Natural Products Chemistry - C; ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1989, vol. 4, p. 431; (c) D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447.
11. For reviews on the asymmetric synthesis of amines and amine derivatives via nonstabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 1, ed. S. L. Schreiber, Pergamon Press, Oxford, 1991, vol. 1, ch. 1.12; (b) E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.3; (c) H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis: Additions to C-C π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.5; (d) J. Klein, in The Chemistry of Double-bonded Functional Groups: Supplement A, ed. S. Patai, John Wiley & Sons, Interscience, Chichester, 1989, vol. 2, part 1, ch. 10.
12. For reviews on the asymmetric synthesis of amines and amine derivatives via nonstabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 1, ed. S. L. Schreiber, Pergamon Press, Oxford, 1991, vol. 1, ch. 1.12; (b) E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.3; (c) H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis: Additions to C-C π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.5; (d) J. Klein, in The Chemistry of Double-bonded Functional Groups: Supplement A, ed. S. Patai, John Wiley & Sons, Interscience, Chichester, 1989, vol. 2, part 1, ch. 10.
13. For reviews on the asymmetric synthesis of amines and amine derivatives via nonstabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 1, ed. S. L. Schreiber, Pergamon Press, Oxford, 1991, vol. 1, ch. 1.12; (b) E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.3; (c) H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis: Additions to C-C π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.5; (d) J. Klein, in The Chemistry of Double-bonded Functional Groups: Supplement A, ed. S. Patai, John Wiley & Sons, Interscience, Chichester, 1989, vol. 2, part 1, ch. 10.
14. For reviews on the asymmetric synthesis of amines and amine derivatives via nonstabilized carbanion additions to the C=N bond of azomethines bearing a chiral auxiliary, see: (a) R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 1, ed. S. L. Schreiber, Pergamon Press, Oxford, 1991, vol. 1, ch. 1.12; (b) E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis: Additions to C-X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.3; (c) H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis: Additions to C-C π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.5; (d) J. Klein, in The Chemistry of Double-bonded Functional Groups: Supplement A, ed. S. Patai, John Wiley & Sons, Interscience, Chichester, 1989, vol. 2, part 1, ch. 10.
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25. For reviews on the use of external chiral ligands in asymmetric synthesis, see: (a) K. Tomioka, Synthesis, 1990, 541; (b) H.-U. Blaser, Chem. Rev., 1992, 92, 935; (c) H. B. Kagan, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1985, vol. 5, ch. 1.
26. For reviews on the use of external chiral ligands in asymmetric synthesis, see: (a) K. Tomioka, Synthesis, 1990, 541; (b) H.-U. Blaser, Chem. Rev., 1992, 92, 935; (c) H. B. Kagan, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1985, vol. 5, ch. 1.
27. For reviews on the use of external chiral ligands in asymmetric synthesis, see: (a) K. Tomioka, Synthesis, 1990, 541; (b) H.-U. Blaser, Chem. Rev., 1992, 92, 935; (c) H. B. Kagan, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, Orlando, 1985, vol. 5, ch. 1.
28. (a) S. E. Denmark, N. Nakajima and O. J.-C. Nicaise, J. Am. Chem. Soc., 1994, 116, 8797;
29. (b) S. E. Denmark, N. Nakajima, O. J.-C. Nicaise, A. M. Faucher and J. P. Edwards, J. Org. Chem., 1995, 60, 4884.
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33. For recent reviews on asymmetric catalysis, see: (a) Catalytic Asymmetric Synthesis. ed. I. Ojima, VCH Verlagsgesellschaft mbH, Weinheim, 1993; (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons Inc., New York, 1994.
34. For recent reviews on asymmetric catalysis, see: (a) Catalytic Asymmetric Synthesis. ed. I. Ojima, VCH Verlagsgesellschaft mbH, Weinheim, 1993; (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons Inc., New York, 1994.
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46. For previous uses of the chiral β-amino ether 3a in various stereoselective reactions by Tomioka and co-workers, see (a) K. Tomioka, M. Sudani, Y. Shinmi and K. Koga, Chem. Lett.. 1985, 329; (b) K. Tomioka, M. Shindo and K. Koga, Chem. Pharm. Bull., 1989, 37, 1120; (c) K. Tomioka, Y. Shinmi, K. Shiina, M. Nakajima and K. Koga, Chem. Pharm. Bull., 1990, 38, 2133.
47. For previous uses of the chiral β-amino ether 3a in various stereoselective reactions by Tomioka and co-workers, see (a) K. Tomioka, M. Sudani, Y. Shinmi and K. Koga, Chem. Lett.. 1985, 329; (b) K. Tomioka, M. Shindo and K. Koga, Chem. Pharm. Bull., 1989, 37, 1120; (c) K. Tomioka, Y. Shinmi, K. Shiina, M. Nakajima and K. Koga, Chem. Pharm. Bull., 1990, 38, 2133.
48. For previous uses of the chiral β-amino ether 3a in various stereoselective reactions by Tomioka and co-workers, see (a) K. Tomioka, M. Sudani, Y. Shinmi and K. Koga, Chem. Lett.. 1985, 329; (b) K. Tomioka, M. Shindo and K. Koga, Chem. Pharm. Bull., 1989, 37, 1120; (c) K. Tomioka, Y. Shinmi, K. Shiina, M. Nakajima and K. Koga, Chem. Pharm. Bull., 1990, 38, 2133.
49. For recent reports by Tomioka and co-workers on the use of other chiral ligands for the catalytic enantioselective addition of other organolithium compounds, see: (a) M. Shindo, K. Koga and K. Tomioka, J. Am. Chem. Soc., 1992, 114, 8732; (b) K. Tomioka, M. Shindo and K. Koga, Tetrahedron Lett., 1993, 34, 681.
50. For recent reports by Tomioka and co-workers on the use of other chiral ligands for the catalytic enantioselective addition of other organolithium compounds, see: (a) M. Shindo, K. Koga and K. Tomioka, J. Am. Chem. Soc., 1992, 114, 8732; (b) K. Tomioka, M. Shindo and K. Koga, Tetrahedron Lett., 1993, 34, 681.
51. (a) S. Itsuno, H. Yanaka, C. Hachisuka and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1991, 1341;
52. (b) S. Itsuno, M. Sasaki, S. Kuroda and K. Ito, Tetrahedron: Asymmetry, 1995, 6, 1507.
53. For a recent example of highly enantioselective addition of Grignard reagents mediated by a chiral diol, see: B. Weber and D. Seebach, Angew. Chem., 1992, 104, 96; Angew. Chem., Int. Ed. Engl., 1992, 31, 84.
54. For a recent example of highly enantioselective addition of Grignard reagents mediated by a chiral diol, see: B. Weber and D. Seebach, Angew. Chem., 1992, 104, 96; Angew. Chem., Int. Ed. Engl., 1992, 31, 84.
55. O. J.-C. Nicaise, Ph.D. Thesis, University of Illinois at Urbana-Champaign, 1993.
56. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
57. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
58. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
59. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
60. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
61. For recent reviews on this topic, see: (a) C. Bolm, Angew. Chem., 1991, 103, 556; Angew. Chem., Int. Ed. Engl., 1991, 30, 542; (b) A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; (c) O. Reiser, Angew. Chem., Int. Ed. Engl., 1993, 32, 547; (d) A. Togni and L. M. Venanzi, Angew. Chem., 1994, 106, 517; Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
62. S. E. Denmark and N. Nakajima, unpublished results.
63. (-)-Sparteine is an inexpensive and commercially available chiral diamine that has found applications in asymmetric transformations of organolithium reagents: (a) H. Nozaki, T. Aratani, T. Takaya and R. Noyori, Tetrahedron, 1971, 27, 905; (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 2403; (c) D. Hoppe, M. Paetow and F. Hinze, Angew. Chem., Int. Ed. Engl., 1993, 32, 394; (d) P. Beak and H. Du, J. Am. Chem. Soc., 1993, 115, 2516; (e) P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
64. (-)-Sparteine is an inexpensive and commercially available chiral diamine that has found applications in asymmetric transformations of organolithium reagents: (a) H. Nozaki, T. Aratani, T. Takaya and R. Noyori, Tetrahedron, 1971, 27, 905; (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 2403; (c) D. Hoppe, M. Paetow and F. Hinze, Angew. Chem., Int. Ed. Engl., 1993, 32, 394; (d) P. Beak and H. Du, J. Am. Chem. Soc., 1993, 115, 2516; (e) P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
65. (-)-Sparteine is an inexpensive and commercially available chiral diamine that has found applications in asymmetric transformations of organolithium reagents: (a) H. Nozaki, T. Aratani, T. Takaya and R. Noyori, Tetrahedron, 1971, 27, 905; (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 2403; (c) D. Hoppe, M. Paetow and F. Hinze, Angew. Chem., Int. Ed. Engl., 1993, 32, 394; (d) P. Beak and H. Du, J. Am. Chem. Soc., 1993, 115, 2516; (e) P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
66. (-)-Sparteine is an inexpensive and commercially available chiral diamine that has found applications in asymmetric transformations of organolithium reagents: (a) H. Nozaki, T. Aratani, T. Takaya and R. Noyori, Tetrahedron, 1971, 27, 905; (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 2403; (c) D. Hoppe, M. Paetow and F. Hinze, Angew. Chem., Int. Ed. Engl., 1993, 32, 394; (d) P. Beak and H. Du, J. Am. Chem. Soc., 1993, 115, 2516; (e) P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
67. (-)-Sparteine is an inexpensive and commercially available chiral diamine that has found applications in asymmetric transformations of organolithium reagents: (a) H. Nozaki, T. Aratani, T. Takaya and R. Noyori, Tetrahedron, 1971, 27, 905; (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 2403; (c) D. Hoppe, M. Paetow and F. Hinze, Angew. Chem., Int. Ed. Engl., 1993, 32, 394; (d) P. Beak and H. Du, J. Am. Chem. Soc., 1993, 115, 2516; (e) P. Beak, S. T. Kerrick, S. Wu and J. Chu, J. Am. Chem. Soc., 1994, 116, 3231.
68. For recent reviews on the chemistry of N-substituted benzotriazoles. see: (a) A. R. Katritzky, S. Rachwal and G. J. Hitchings, Tetrahedron, 1991, 47, 2683; (b) A. R. Katritzky, Bull. Soc. Chim. Belg., 1992, 101, 409.
69. For recent reviews on the chemistry of N-substituted benzotriazoles. see: (a) A. R. Katritzky, S. Rachwal and G. J. Hitchings, Tetrahedron, 1991, 47, 2683; (b) A. R. Katritzky, Bull. Soc. Chim. Belg., 1992, 101, 409.
70. A. R. Katritzky and P. A. Harris, Tetrahedron: Asymmetry, 1992, 3, 437.
71. K. Soai, T. Hatanaka and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097.
72. Y. Ukaji, T. Hatanaka, A. Ahmed and K. Inomata, Chem. Lett., 1993, 1313; Ukaji and Inomata have recently described a catalytic variant of this reaction which proceeds in 56-70% ee: Y. Ukaji, Y. Kenmuoku and K. Inomata, Tetrahedron: Asymmetry, 1996, 7, 53.
73. Y. Ukaji, T. Hatanaka, A. Ahmed and K. Inomata, Chem. Lett., 1993, 1313; Ukaji and Inomata have recently described a catalytic variant of this reaction which proceeds in 56-70% ee: Y. Ukaji, Y. Kenmuoku and K. Inomata, Tetrahedron: Asymmetry, 1996, 7, 53.
74. For recent examples of asymmetric synthesis of chiral amines by catalytic reduction, see: (a) M. J. Burk, J. P. Martinez, J. E. Feaster and N. Cosford, Tetrahedron, 1994, 50, 4399; (b) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 11 703 and references cited therein.
75. For recent examples of asymmetric synthesis of chiral amines by catalytic reduction, see: (a) M. J. Burk, J. P. Martinez, J. E. Feaster and N. Cosford, Tetrahedron, 1994, 50, 4399; (b) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 11 703 and references cited therein.