Silver/ThioClickFerrophos-catalyzed enantioselective conjugate addition and cycloaddition of glycine imino ester with nitroalkenes.
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.
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Tokyo 112-8551, Japan.
Kazumi
K
Imae
Takashi
T
Konno
Kenichi
K
Ogata
Shin-ichi
S
Fukuzawa
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005296:Ferrous Compounds / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry
D000475:Alkenes; D004952:Esters; D005296:Ferrous Compounds; D007097:Imines; D009574:Nitro Compounds; D009942:Organometallic Compounds; D011759:Pyrrolidines; D014230:Triazoles; D012834:Silver; D005998:Glycine