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  • Title: A highly stereoselective synthesis of optically active trisubstituted 1,2-ethylenediamines: the first example of grignard addition to N-diphenylphosphinoyl ketimines derived from amino acids.
    Author: Kohmura Y, Mase T.
    Journal: J Org Chem; 2004 Sep 17; 69(19):6329-34. PubMed ID: 15357592.
    Abstract:
    The efficient synthesis of optically active trisubstituted 1,2-ethylenediamines is described. Addition of aryl and/or alkyl Grignard reagents to alpha-amino N-diphenylphosphinoyl ketimines derived from alpha-amino acids was demonstrated to afford the desired trisubstituted 1,2-ethylenediamines in good yields and with high diastereoselectivities. Subsequent removal of the diphenyphosphinoyl group from the adduct was smoothly accomplished in reasonable yield without racemization under newly developed reductive conditions.
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