Enantioselective Borane Catalyzed Reduction of Imines

Synlett

Volumn 1996, Issue 2, 1996, Pages 177-178

  Brunel, Jean Michel ^a   Buono, Gérard ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542527227     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5343     Document Type: Article

References (31)

1. For some reviews on the asymmetric reduction of ketones, see : (a) Walbaum, S.; Martens, J. Tetrahedron Asymmetry 1992, 3, 1475. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. (c) Singh, V. K. Synthesis 1992, 605.
2. For some reviews on the asymmetric reduction of ketones, see : (a) Walbaum, S.; Martens, J. Tetrahedron Asymmetry 1992, 3, 1475. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. (c) Singh, V. K. Synthesis 1992, 605.
3. For some reviews on the asymmetric reduction of ketones, see : (a) Walbaum, S.; Martens, J. Tetrahedron Asymmetry 1992, 3, 1475. (b) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763. (c) Singh, V. K. Synthesis 1992, 605.
4. Jacques, J.; Collet, A.; Wilen, S. H. in "Enantiomers, Racemates, and Resolution" J. Wiley and sons, Ed. New York, NY 1981.
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30. 4 and then distilled on a Kugelrohr apparatus to afford amine 3a in an average yield of 62%.
31. Recently, it was reported that the isomerisation of the imine has an effect on the enantioselectivity of the reaction. Such a hypothesis cannot be excluded to explain our results. Chan, A. S. C.; Chen, C.; Lin, C.; Lin, Y.; Cheng, M.; Peng, S. J. Chem. Soc., Chem. Commun. 1995, 1767.