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Synlett 1994; 1994(12): 1054-1056
DOI: 10.1055/s-1994-23083
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Enantioselective Synthesis of α-Substituted Nitriles by Oxidative Cleavage of Aldehyde SAMP-Hydrazones with Magnesium Monoperoxyphthalate

D. Enders* , A. Plant
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany
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Publication Date:
22 March 2002 (online)

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A practical asymmetric synthesis of α-substituted nitriles of high enantiomeric purity (ee = > 90 - ≥ 96 %) based on the SAMP/RAMP-hydrazone method is described. Key step is the racemization free magnesium monoperphthalate (MMPP)-mediated aza Cope elimination of aldehyde SAMP-hydrazones to generate the CN triple bond. 4-Cyano-esters obtained by Michael addition can be converted into cis-4,5-disubstituted piperidin-2-ones (de, ee ≥ 92 %).

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