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  • Title: Silver/ThioClickFerrophos-catalyzed enantioselective conjugate addition and cycloaddition of glycine imino ester with nitroalkenes.
    Author: Imae K, Konno T, Ogata K, Fukuzawa S.
    Journal: Org Lett; 2012 Sep 07; 14(17):4410-3. PubMed ID: 22900645.
    Abstract:
    We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-α-imino-γ-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 °C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.
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