Organocatalysis with a fluorous tag: Asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides

Malkov, A. V., Figlus, M., Stoncius, S. and Kocovsky, P. . (2007) Organocatalysis with a fluorous tag: Asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides. Journal of Organic Chemistry, 72(4), pp. 1315-1325. (doi: 10.1021/jo062215i)

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Publisher's URL: http://dx.doi.org/10.1021/jo062215i

Abstract

Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3a−d with high enantioselectivity (≤95% ee) and low catalyst loading (1−5 mol %) at room temperature in toluene. Appending a fluorous tag, as in 5a−c, simplifies the isolation procedure, while preserving high enantioselectivity (≤92% ee).

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Figlus, M., Stoncius, S., and Kocovsky, P. .
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:18 January 2007

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
370221New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric CatalysisAndrei MalkovEngineering & Physical Sciences Research Council (EPSRC)GR/S87294/01Chemistry