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  • Title: An expedient and practical method for the synthesis of a diverse series of cyclopropane alpha-amino acids and amines.
    Author: Wurz RP, Charette AB.
    Journal: J Org Chem; 2004 Feb 20; 69(4):1262-9. PubMed ID: 14961679.
    Abstract:
    A practical synthesis for the preparation of a diverse series of cyclopropane alpha-amino acids is described. Nitrocyclopropane carboxylates can be readily prepared through treatment of alpha-nitroesters and iodobenzene diacetate or alpha-nitro-alpha-diazoesters with a Rh(II) catalyst and an olefin. Reduction of the nitro group using zinc/HCl in i-PrOH affords substituted cyclopropane alpha-amino esters in modest to high yields (54-99%). A "one-pot" procedure involving sequential cyclopropanation and reduction is described. The method can also be applied to the preparation of arylcyclopropyl amines (three examples).
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