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  • Title: Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands.
    Author: Panella L, Aleixandre AM, Kruidhof GJ, Robertus J, Feringa BL, de Vries JG, Minnaard AJ.
    Journal: J Org Chem; 2006 Mar 03; 71(5):2026-36. PubMed ID: 16496990.
    Abstract:
    Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol % catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions.
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