A Practical Method for Asymmetric Borane Reduction of Prochiral Ketones Using Chiral Amino Alcohols and Trimethyl Borate

Synlett

Volumn 1997, Issue 3, 1997, Pages 273-274

  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: 0002636206     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-779     Document Type: Article

References (15)

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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. (c) 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. (c) 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. (c) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475. (d)Singh, V. K. Synthesis 1992, 605.
5. Masui, M.; Shioiri, T. Tetrahedron 1995, 51, 8363.
6. Masui, M.; Shioiri, T. Synlett 1996, 49.
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8. 2 at room temperature for 1 h. After borane-dimethyl sulfide complex (3.5-10 mmol) was added, a solution of ketone (5 mmol) in 5 ml of dry THF was added dropwise via a syringe pump over 1 h. The reaction mixture was stirred until the ketone disappeared on a thin layer chromatography. The resulting mixture was quenched with 2N HCI. Usual workup provided the chiral alcohol.
9. Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 785.
10. Seemayer, R.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 827.
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