Asymmetric Borane Reduction of Prochiral Ketones with Oxazaborolidines Derived from α-Pinene

Synlett

Volumn 1996, Issue 1, 1996, Pages 49-50

  Masui, Moriyasu ^a   Shioiri, Takayuki ^b  

^a SHIONOGI AND CO LTD   (Japan)

^b NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347528442     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5331     Document Type: Article

References (17)

1. For recent reviews, see: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475. (d) Singh, V. K. Synthesis 1992, 605.
2. For recent reviews, see: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475. (d) Singh, V. K. Synthesis 1992, 605.
3. For recent reviews, see: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475. (d) Singh, V. K. Synthesis 1992, 605.
4. For recent reviews, see: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475. (d) Singh, V. K. Synthesis 1992, 605.
5. Isuno, S.; Sakurai, Y; Ito, K.; Hirao, A.; Nakahama, S.; Bull. Chem. Soc. Jpn. 1987, 60, 395, and references therein.
6. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Org. Chem. 1988, 53, 2861, and references therein.
7. Rama Rao, A. V.; Gurjar, M. K.; Sharma, P. A.; Kaiwar, V. Tetrahedron Lett. 1990, 31, 2341.
8. Rama Rao, A, V; Gurjar, M. K.; Kaiwar, V. Tetrahedron: Asymmetry 1992, 3, 859.
9. (a) Quallich, G. J., Woodall, T. M. Synlett 1993, 929.
10. (b) Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 4145.
11. (a) Simone, B. D.; Savoia, D.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1995, 6, 301.
12. (b) Hong, Y; Gao, Y; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631.
13. Masui, M.; Shioiri, T. Tetrahedron 1995, 51, 8363.
14. 4, and concentrated in vacuo. The residue was purified on a silica gel column chromatography provided the chiral alcohol.
15. Preparation of 3d was achieved by the addition of 1 ml of 10 M borane-methyl sulfide complex to a solution of the aminoalcohol 1 (Immol) in 5 ml of dry THF and the mixture was stirred at room temperature for 1 h. The resulting mixture was used in the asymmetric reduction described in reference 9.
16. Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799.
17. Quallich, G. J.; Blake, J. F.; Woodall, T. M. J. Am. Chem. Soc. 1994, 116, 8516.