A Convenient Method for the Synthesis of Bis(trialkylphosphine)-Boranes Bearing Two Phospholanes

Synlett

Volumn 1996, Issue 12, 1996, Pages 1211-1212

  Morimoto, Toshiaki ^a   Ando, Naoki ^a   Achiwa, Kazuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002826722     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5728     Document Type: Article

References (26)

1. Reviews: (a) Takahashi, H.; Morimoto, T.; Achiwa, K. Yuki Gousei Kagaku Kyokai Shi, 1990, 48, 29. (b) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett, 1992, 169.
2. Reviews: (a) Takahashi, H.; Morimoto, T.; Achiwa, K. Yuki Gousei Kagaku Kyokai Shi, 1990, 48, 29. (b) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett, 1992, 169.
3. (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett., 1986, 27, 4477 (1986).
4. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett., 1986, 2061.
5. (c) Chiba, M.; Takahashi, H.; Takahashi, H.; Morimoto, T.; Achiwa, K. Tetrahedron Lett., 1987, 28, 3675.
6. (a) Tani, K.; Ise, T.; Tatsuno, Y.; and Ito, T.J. Chem. Soc., Chem. Commun., 1984, 1641.
7. (b) Tani, K.; Suwa, E.; E. Tanigawa, E.; Ise, T.; Yamagata, T.; Tatsuno, Y.; Otsuka, S. J. Organomet. Chem., 1989, 203.
8. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics, 1990, 10, 2653 (1990).
9. (b) Burk, M. J.; Harlow, R. L. Angew. Chem. Int. Ed. Engl., 1990, 29, 1462.
10. (c) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron Asymmetry, 1991, 21, 569.
11. (d) Burk, M. J. J. Am. Chem. Soc., 1991, 113, 8518.
12. (e) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc., 1993, 115, 10125.
13. (f) Burk M. J.; Feaster, J. E. J. Am. Chem. Soc., 1992, 114, 6266.
14. (g) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc., 1995, 117, 4423.
15. (h) Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am. Chem. Soc., 1995, 117, 8277.
16. (i) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc., 1995, 117, 9375.
17. (j) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc., 1996, 118, 5142.
18. 2O (500 ml) in the presence of Lipase AH (Amano) gave (2R,5R)-2,5-hexanediol diacetyl ester (11 g, 28% yield) with 96% ee. The meso diol in the mixture was transformed into the corresponding optically active half ester, which could be converted to the (2R,5R)-diacetate by inversion of configuration of the hydroxy group employing the Mitsunobu reaction. The optically active diacetate was hydrolyzed to the corresponding diol, which was purified to 100% ee by recrystallization from ether [Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289.]. (Matrix Presented) Other efficient preparative methods for the diol have been reported [Ikeda, H.; Sato, E.; Sugai, T.; Ohta, H. Tetrahedron, 1996, 52, 8113 and references cited therein.].
19. 2O (500 ml) in the presence of Lipase AH (Amano) gave (2R,5R)-2,5-hexanediol diacetyl ester (11 g, 28% yield) with 96% ee. The meso diol in the mixture was transformed into the corresponding optically active half ester, which could be converted to the (2R,5R)-diacetate by inversion of configuration of the hydroxy group employing the Mitsunobu reaction. The optically active diacetate was hydrolyzed to the corresponding diol, which was purified to 100% ee by recrystallization from ether [Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289.]. (Matrix Presented) Other efficient preparative methods for the diol have been reported [Ikeda, H.; Sato, E.; Sugai, T.; Ohta, H. Tetrahedron, 1996, 52, 8113 and references cited therein.].
20. Borane complexes of aryl-substituted phosphines were used for the preparation of various trisubstituted phosphine-boranes including chiral phosphine ligands [Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc., 1990, 122, 5244. Brisset, H.; Gourdel, Y.; Pellon, P.; Corre, M. L. Tetrahedron Lett., 1993, 34, 4523.].
21. Borane complexes of aryl-substituted phosphines were used for the preparation of various trisubstituted phosphine-boranes including chiral phosphine ligands [Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc., 1990, 122, 5244. Brisset, H.; Gourdel, Y.; Pellon, P.; Corre, M. L. Tetrahedron Lett., 1993, 34, 4523.].
22. Lithium phosphide is known to react with THF or ethers [Issleib, K.; Mobius, H. M. Chem. Ber., 1961, 94, 102. Mallion, K. B. Chem. Ind., 1963, 654; Garmer A. Y.; Tedeschi, A. A. J. Am. Chem. Soc., 1962, 84, 4737. Schindlbauer, H. Monatsh. Chem., 1965, 96, 961.].
23. Lithium phosphide is known to react with THF or ethers [Issleib, K.; Mobius, H. M. Chem. Ber., 1961, 94, 102. Mallion, K. B. Chem. Ind., 1963, 654; Garmer A. Y.; Tedeschi, A. A. J. Am. Chem. Soc., 1962, 84, 4737. Schindlbauer, H. Monatsh. Chem., 1965, 96, 961.].
24. Lithium phosphide is known to react with THF or ethers [Issleib, K.; Mobius, H. M. Chem. Ber., 1961, 94, 102. Mallion, K. B. Chem. Ind., 1963, 654; Garmer A. Y.; Tedeschi, A. A. J. Am. Chem. Soc., 1962, 84, 4737. Schindlbauer, H. Monatsh. Chem., 1965, 96, 961.].
25. Lithium phosphide is known to react with THF or ethers [Issleib, K.; Mobius, H. M. Chem. Ber., 1961, 94, 102. Mallion, K. B. Chem. Ind., 1963, 654; Garmer A. Y.; Tedeschi, A. A. J. Am. Chem. Soc., 1962, 84, 4737. Schindlbauer, H. Monatsh. Chem., 1965, 96, 961.].
26. 3). The analytical and spectral data of 8, 10 were also well consistent with their structures.