beta-nitrostyrene, (E)- → (1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-phenylcyclopentanecarboxylate

Participants

Reaction Steps

To a solution of 6-benzyl 1-ethyl 5-acetylhex-2-enedioate 4b (0.3 mmol, 1.0 eq) and 1-((E)-2-nitrovinyl)benzene (0.45 mmol, 1.5 eq) in diethylether (0.4 mL) was added catalyst VI (Q-NH2) (0.045 mmol, 0.15 eq) at room temperature (22° C.). The resulting mixture was stirred vigorously for 16 hours, then the reaction was continued for about 6 hours after removal of the solvent. After the reaction was completed (monitored by TLC and crude NMR), the title product was afforded by flash chromatography over silica gel (Ethyl acetate:Hexane=1:10 to 1:4) in 91% yield.

Provenance & Evidence