Enantioselective Synthesis of α-Substituted Nitriles by Oxidative Cleavage of Aldehyde SAMP-Hydrazones with Magnesium Monoperoxyphthalate

1 January 1994

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1994 (12) , 1054-1056
https://doi.org/10.1055/s-1994-23083

Abstract

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 %).

Keywords

MAGNESIUM

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