Inorganic carbonates as nucleophiles for the asymmetric synthesis of vinylglycidols [3]

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8649-8650

  Trost, Barry M ^a   McEachern, Ernest J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; CARBONIC ACID DERIVATIVE; EPOXIDE; GLYCIDOL; INORGANIC COMPOUND; ISOPRENE; WATER;

CATALYSIS; CHEMICAL REACTION KINETICS; LETTER; OLIGOMERIZATION; RACEMIC MIXTURE; SYNTHESIS;

EID: 0033595445     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990783s     Document Type: Letter

References (25)

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4. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
5. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
6. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
7. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
8. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
9. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
10. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
11. For some applications, see: Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959; Gurjar, M. K.; Devi, N. R. Tetrahedron: Asymmetry 1994, 5, 755; Rao, A. V.; Hurjar, M. K.; Bose, D. S.; Devi, R. R. J. Org. Chem. 1991, 56, 1320; Jäger, V.; Schröter, D. Synthesis 1990, 556; Rama Rao, A. V.; Subhas, D.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031; Walkup, R. D.; Cunningham, R. T. Tetrahedron Lett. 1987, 28, 4019; Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880; Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 22, 2859.
12. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
13. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
14. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
15. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
16. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
17. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
18. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
19. For a kinetic resolution from butadiene monoepoxide, see: Tokunaga, M.; Larrow, J. F.; Kakuichi, F.; Jacobsen, E. N. Science 1997, 277, 936. For enzymatic kinetic resolution of the diol, see Boaz, N. W.; Zimmerman, R. L. Tetrahedron: Asymmetry 1994, 5, 153; Suzuki, T.; Kasai, N.; Minamuira, N. Tetrahedron: Asymmetry 1994, 5, 239; Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765. For asymmetric synthesis, see: ref 3 and Saibata, R.; Sarma, M. S. P.; Abushnab, E. Synth. Commun. 1989, 19, 3077; Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447; Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599.
20. Cf. Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. Fujiname, T.; Suzuki, T.; Kamiya, M.; Fukazawa, S.-I.; Sakai, S. Chem. Lett. 1985, 199. Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Bull. Chem. Soc. Jpn. 1999, 72, 1063.
21. Cf. Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. Fujiname, T.; Suzuki, T.; Kamiya, M.; Fukazawa, S.-I.; Sakai, S. Chem. Lett. 1985, 199. Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Bull. Chem. Soc. Jpn. 1999, 72, 1063.
22. Cf. Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. Fujiname, T.; Suzuki, T.; Kamiya, M.; Fukazawa, S.-I.; Sakai, S. Chem. Lett. 1985, 199. Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Bull. Chem. Soc. Jpn. 1999, 72, 1063.
23. Suzuki, M.; Watanabe, A.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 2095; Suzuki, M.; Oda, Y.; Noyori, R. ibid. 1979, 101, 1623.
24. Suzuki, M.; Watanabe, A.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 2095; Suzuki, M.; Oda, Y.; Noyori, R. ibid. 1979, 101, 1623.
25. Howes, D. A.; Brookes, M. H.; Coates, D.; Golding, B. T.; Hudson, A. T. J. Chem. Res. (M) 1983, 1, 217.