Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic method

Angewandte Chemie - International Edition

Volumn 37, Issue 15, 1998, Pages 1986-2012

  Corey, Elias J ^a   Helal, Christopher J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Boron; Ketones; Reductions; Total synthesis

Indexed keywords

EID: 0032541271     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z     Document Type: Review

References (193)

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45. For improved preparations of amino alcohol 3, see a) D. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751-762; b) J. V. B. Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127-5132; c) for an earlier review of oxazaborolidine-catalyzed reduction of ketones, see V. K. Singh, Synthesis 1992, 605-616.
46. For improved preparations of amino alcohol 3, see a) D. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751-762; b) J. V. B. Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127-5132; c) for an earlier review of oxazaborolidine-catalyzed reduction of ketones, see V. K. Singh, Synthesis 1992, 605-616.
47. For improved preparations of amino alcohol 3, see a) D. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751-762; b) J. V. B. Kanth, M. Periasamy, Tetrahedron 1993, 49, 5127-5132; c) for an earlier review of oxazaborolidine-catalyzed reduction of ketones, see V. K. Singh, Synthesis 1992, 605-616.
48. J. O. Link, Ph.D. thesis, Harvard University (USA), 1992.
49. [13a]
50. 2S to effect the enantioselective reduction of ketones:
51. b) D. J. Mathre, A. S. Thompson, A. W. Douglas, K. Hoogsteen, J. D. Carroll, E. G. Corley, E. J. J. Grabowski, J. Org. Chem. 1993, 58, 2880-2888.
52. It has not been proven if the hydride transfer occurs via a boat or a chair transition state. Both conformations, however, are consistent with the mechanistic model in Scheme 5: a) D. A. Evans, Science 1988, 240, 420-426; for computational studies, see b) D. K. Jones, D. C. Liotta, I. Shinkai, D. J. Mathre, J. Org. Chem. 1993, 58, 799-801; c) L. P. Linney, C. R. Self, I. H. Williams, J. Chem. Soc. Chem. Commun. 1994, 1651-1652; for computational studies concerning different oxazaborolidines, see d) G. J. Quallich, J. F. Blake, T. M. Woodall, J. Am. Chem. Soc. 1994, 116, 8516-8525.
53. It has not been proven if the hydride transfer occurs via a boat or a chair transition state. Both conformations, however, are consistent with the mechanistic model in Scheme 5: a) D. A. Evans, Science 1988, 240, 420-426; for computational studies, see b) D. K. Jones, D. C. Liotta, I. Shinkai, D. J. Mathre, J. Org. Chem. 1993, 58, 799-801; c) L. P. Linney, C. R. Self, I. H. Williams, J. Chem. Soc. Chem. Commun. 1994, 1651-1652; for computational studies concerning different oxazaborolidines, see d) G. J. Quallich, J. F. Blake, T. M. Woodall, J. Am. Chem. Soc. 1994, 116, 8516-8525.
54. It has not been proven if the hydride transfer occurs via a boat or a chair transition state. Both conformations, however, are consistent with the mechanistic model in Scheme 5: a) D. A. Evans, Science 1988, 240, 420-426; for computational studies, see b) D. K. Jones, D. C. Liotta, I. Shinkai, D. J. Mathre, J. Org. Chem. 1993, 58, 799-801; c) L. P. Linney, C. R. Self, I. H. Williams, J. Chem. Soc. Chem. Commun. 1994, 1651-1652; for computational studies concerning different oxazaborolidines, see d) G. J. Quallich, J. F. Blake, T. M. Woodall, J. Am. Chem. Soc. 1994, 116, 8516-8525.
55. It has not been proven if the hydride transfer occurs via a boat or a chair transition state. Both conformations, however, are consistent with the mechanistic model in Scheme 5: a) D. A. Evans, Science 1988, 240, 420-426; for computational studies, see b) D. K. Jones, D. C. Liotta, I. Shinkai, D. J. Mathre, J. Org. Chem. 1993, 58, 799-801; c) L. P. Linney, C. R. Self, I. H. Williams, J. Chem. Soc. Chem. Commun. 1994, 1651-1652; for computational studies concerning different oxazaborolidines, see d) G. J. Quallich, J. F. Blake, T. M. Woodall, J. Am. Chem. Soc. 1994, 116, 8516-8525.
56. For the initial report proposing the direct conversion of 7 into 5, see a) reference [13a]; for computational studies, see b) V. Nevalainen, Tetrahedron: Asymmetry 1994, 5, 289-296; c) reference [18c].
57. For the initial report proposing the direct conversion of 7 into 5, see a) reference [13a]; for computational studies, see b) V. Nevalainen, Tetrahedron: Asymmetry 1994, 5, 289-296; c) reference [18c].
58. For the initial report proposing the direct conversion of 7 into 5, see a) reference [13a]; for computational studies, see b) V. Nevalainen, Tetrahedron: Asymmetry 1994, 5, 289-296; c) reference [18c].
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61. For studies detailing the role of the borinate 8 in effecting product enantioselectivity, see a) D. M. Tschaen, L. Abramson, D. Cai, R. Desmond, U.-H. Dolling, L. Frey, S. Karady, Y.-J. Shi, T. R. Verhoeven, J. Org. Chem. 1995, 60, 4324-4330; b) Y.-J. Shi, D. Cai, U-H. Dolling, A. W. Douglas, D. M. Tschaen, T. R. Verhoeven, Tetrahedron Lett. 1994, 55, 6409-6412.
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63. 2 > p-H > p-MeO.
64. [18c]
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67. R = H: a) A. V. Rama Rao, M. K. Gurjar, V. Kaiwar, Tetrahedron: Asymmetry 1992, 3, 859-862; b) W. Behnen, C. Dauelsberg, S. Wallbaum, J. Martens, Synth. Commun. 1992, 22, 2143-2153; R = Me: c) E. J. Corey, V. K. Singh, unpublished results.
68. R = H: a) A. V. Rama Rao, M. K. Gurjar, V. Kaiwar, Tetrahedron: Asymmetry 1992, 3, 859-862; b) W. Behnen, C. Dauelsberg, S. Wallbaum, J. Martens, Synth. Commun. 1992, 22, 2143-2153; R = Me: c) E. J. Corey, V. K. Singh, unpublished results.
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72. R = H: a) Y. H. Kim, D. H. Park, I. S. Byun, I. K. Yoon, C. S. Park, J. Org. Chem. 1993, 58, 4511-4512; b) J. Martens, C. Dauelsberg, W. Behnen, S. Wallbaum, Tetrahedron: Asymmetry 1992, 3, 347-350. R = Me: c) reference [25c].
73. R = H: a) Y. H. Kim, D. H. Park, I. S. Byun, I. K. Yoon, C. S. Park, J. Org. Chem. 1993, 58, 4511-4512; b) J. Martens, C. Dauelsberg, W. Behnen, S. Wallbaum, Tetrahedron: Asymmetry 1992, 3, 347-350. R = Me: c) reference [25c].
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79. E. J. Corey, S. Shibata, unpublished results.
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81. [33]
82. E. J. Corey, J. O. Link, unpublished results.
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88. E. J. Corey, R. K. Bakshi, S. Shibata, unpublished results.
89. E. J. Corey, C.-P. Chen, R. K. Bakshi, S. Shibata, unpublished results.
90. E. J. Corey, K. Y. Yi, S. P. T. Matsuda, Tetrahedron Lett. 1992, 33, 2319-2322.
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92. a) E. J. Corey, C. J. Helal, unpublished results;
93. b) a number of oxazaborolidine catalysts with p-substituted aryl groups on the boron atom of the catalyst have been prepared : T. K. Jones, J. J. Mohan, L. C. Xavier, T. J. Blacklock, D. J. Mathre, P. Sohar, E. T. Turner Jones, R. A. Reamer, F. E. Roberts, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 763-769.
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97. For a recent in situ preparation of catecholborane, see Y. Suseela, M. Periasamy, J. Organomet. Chem. 1993, 450, 47-52.
98. 3): δ = 28.3; E. J. Corey, K. A. Cimprich, C. J. Helal, unpublished results.
99. Numerous in situ preparations of B-H-4 have recently been reported which result in excellent enantioselectivity for the reduction of a number of different ketones, but which do not provide physical characterization of the catalyst system: a) M. Masui, T. Shioiri, Synlett 1997, 273-274; b) K. R. K. Prasad, N. N. Joshi, Tetrahedron: Asymmetry 1996, 7, 3147-3152; c) M. Periasamy, J. V. B. Kanth, A. S. B. Prasad, Tetrahedron 1994, 50, 6411-6416; d) G. J. Quallich, T. M. Woodall, Synlett 1993, 929-930.
100. Numerous in situ preparations of B-H-4 have recently been reported which result in excellent enantioselectivity for the reduction of a number of different ketones, but which do not provide physical characterization of the catalyst system: a) M. Masui, T. Shioiri, Synlett 1997, 273-274; b) K. R. K. Prasad, N. N. Joshi, Tetrahedron: Asymmetry 1996, 7, 3147-3152; c) M. Periasamy, J. V. B. Kanth, A. S. B. Prasad, Tetrahedron 1994, 50, 6411-6416; d) G. J. Quallich, T. M. Woodall, Synlett 1993, 929-930.
101. Numerous in situ preparations of B-H-4 have recently been reported which result in excellent enantioselectivity for the reduction of a number of different ketones, but which do not provide physical characterization of the catalyst system: a) M. Masui, T. Shioiri, Synlett 1997, 273-274; b) K. R. K. Prasad, N. N. Joshi, Tetrahedron: Asymmetry 1996, 7, 3147-3152; c) M. Periasamy, J. V. B. Kanth, A. S. B. Prasad, Tetrahedron 1994, 50, 6411-6416; d) G. J. Quallich, T. M. Woodall, Synlett 1993, 929-930.
102. Numerous in situ preparations of B-H-4 have recently been reported which result in excellent enantioselectivity for the reduction of a number of different ketones, but which do not provide physical characterization of the catalyst system: a) M. Masui, T. Shioiri, Synlett 1997, 273-274; b) K. R. K. Prasad, N. N. Joshi, Tetrahedron: Asymmetry 1996, 7, 3147-3152; c) M. Periasamy, J. V. B. Kanth, A. S. B. Prasad, Tetrahedron 1994, 50, 6411-6416; d) G. J. Quallich, T. M. Woodall, Synlett 1993, 929-930.
103. [14a]
104. 2, see
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111. 3 · THF (BTHF).
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114. R: 17.7 min, major; 23 min, minor isomer.
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