Chiral allylic and allenic stannanes as reagents for asymmetric synthesis

Chemical Reviews

Volumn 96, Issue 1, 1996, Pages 31-47

  Marshall, James A ^a,b  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002313620     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr950037f     Document Type: Article

References (72)

1. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
2. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
3. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
4. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
5. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
6. For overviews and summaries of synthetic strategies, see: (a) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1987, 26, 489. (b) Hoffmann, R. W.; Dakmann, G.; Andersen, M. W. Synthesis, 1994, 629. (c) Andersen, M. W.; Hildebrandt, B.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 97. (d) Roush, W. R. J. Org. Chem. 1991, 56, 4151. (e) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
7. Reviews: (a) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Clarendon Press: Oxford, 1988; pp 73-310. (b) Baggett, N. In Carbohydrate Chemistry; Kennedy, J. F.; Clarendon Press: Oxford, 1988; pp 379-442.
8. Reviews: (a) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Clarendon Press: Oxford, 1988; pp 73-310. (b) Baggett, N. In Carbohydrate Chemistry; Kennedy, J. F.; Clarendon Press: Oxford, 1988; pp 379-442.
9. Reviews: (a) Masamune, M.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (b) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238. (c) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 239-275.
10. Reviews: (a) Masamune, M.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (b) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238. (c) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 239-275.
11. Reviews: (a) Masamune, M.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. (b) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238. (c) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 239-275.
12. Reviews: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53.
13. Eliel, E., in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando; 1983; Vol. 2, pp 125-155.
14. Compare: Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
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45. γ-Methoxy allyl boronates react at 6-8 kbar with lactaldehyde derivatives to give methoxy cyclopropanes as the major products: Hoffmann, R. W.; Metternich, R. Liebigs. Ann. Chem. 1985, 2390. We thank Professor Hoffmann for calling our attention to this work.
46. Relative rate is not always a reliable criterion of matching and mismatching, as the slower reacting pair of chiral reactants have on occasion been found to be matched and vice versa: Van Nieuwenhze, M. S.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7864.
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55. For a recent review: Thomas, E. J. Chemtracts-Org. Chem. 1994, 7, 207.
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57. For a review: Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 932.
58. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
59. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 3211.
60. For previous work in this area, see: Ruitenberg, K.; Westmijze, H.; Kleijn, H.; Vermeer, P. J. Organomet. Chem. 1984, 277, 227.
61. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1990, 55, 6246.
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64. Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556.
65. The terms "syn" and "anti" refer to the relationship between the δ-allenic and the α-carbinyl hydrogens of the allenylcarbinols.
66. Marshall J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550.
67. Review: Boivin, T. B. L. Tetrahedron 1987, 43, 3309.
68. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
69. Marshall, J. A.; Tang, Y. Synlett 1992, 653.
70. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Kreshnamurthy, D.; Greier, M. J. Org. Chem. 1993, 58, 6543.
71. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Kreshnamurthy, D.; Greier, M. J. Org. Chem. 1993, 58, 6543.
72. Work in progress with Richard Yu.