char = A;code = 65
Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N-(tert-butanesulfinyl)ketimines.char = T;code = 84
Publication: J. Org. Chem. 2010 Aug 6 ;75(15)::5265-70. :doi: 10.1021/jo101057s.
Publication Date: 2010 Aug 6
Study Author(s): Guijarro, David;Pablo, Oscar;Yus, Miguel;
Institution: Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.
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The diastereoselective reduction of (R)-N-(tert-butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched alpha-branched primary amines (up to >99% ee) in short reaction times (1-4 h). (1S,2R)-1-Amino-2-indanol has been shown to be a very efficient ligand to perform this transformation. Ketimines bearing either an aryl or a heteroaryl group and an alkyl group as substituents of the iminic carbon atom are very good substrates for this process. The reduction of a dialkyl ketimine could also be achieved, affording the expected amine with moderate optical purity (69% ee). Some amines which are precursors of very interesting biologically and pharmacologically active compounds have been prepared in excellent yields and enantiomeric excesses.
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