Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands

…, AM Aleixandre, GJ Kruidhof, J Robertus…

Index: Panella, Lavinia; Aleixandre, Alicia Marco; Kruidhof, Gerlof J.; Robertus, Jort; Feringa, Ben L.; De Vries, Johannes G.; Minnaard, Adriaan J. Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 2026 - 2036

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Citation Number: 63

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 ...