Evolution of titanium(IV) alkoxides and Raney Nickel for asymmetric reductive amination of prochiral aliphatic ketones

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4967-4970

  Nugent, Thomas C ^a   Wakchaure, Vijay N ^a   Ghosh, Abhijit K ^a   Mohanty, Rashmi R ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27644565224     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051909v     Document Type: Article

References (44)

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26. 4 (99.999%).
27. In all instances the major amine diastereomer, (R,R)-2, could be isolated in analytically pure form using flash chromatography.
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32. Reference 14b does not provide the yield for the imine step. Based on ref 5f it is assumed to be 85%.
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35. A brief examination of the Raney Ni literature revealed that catalyst loadings vary widely for both imine reduction and reductive amination protocols. The following turnover numbers (defined as millimole of starting substrate per gram of Raney Ni) were calculated: 4.9, 6.7 and 8, 20, 25, 29, 75, 80; see the respective references. It should be noted that the very good turnover numbers, 75 and 80, required a large excess of amine or ketone, and at room temperature 5 d were required for full reaction, while at 80°C fast reactions occurred, (a) Huffmann, M. A.; Reider, P. J. Tetrahedron Lett. 1999, 40, 831.
36. (b) Process for producing optically active benzene-sulfonamide derivatives. Okado, M.; Oshida, K. Y.; Takanobu, K.; Yamanouchi Pharmaceutical Co, Ltd., Japan. Patent IE63344, 1995.
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