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  • Title: Synthesis of gamma-amino esters via Mn-mediated radical addition to chiral gamma-hydrazonoesters.
    Author: Friestad GK, Banerjee K.
    Journal: Org Lett; 2009 Mar 05; 11(5):1095-8. PubMed ID: 19199819.
    Abstract:
    Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.
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