alpha-Alkylation, 3-(6-(benzyloxy)benzo[d][1,3]dioxol-5-yl)-1-((5-(trifluoromethyl)furan-2-yl)methyl)indolin-2-one, ((chloromethoxy)methyl)benzene, (S)-3-(6-(benzyloxy)benzo[d][1,3]dioxol-5-yl)-3-((benzyloxy)methyl)-1-((5-(trifluoromethyl)furan-2-yl)methyl)indolin-2-one, (9S)-1-(9-anthracenylmethyl)-9-hydroxy-cinchonanium chloride, Cinchonine Derivative
Allylation, 2-phenylpropanal, 1-phenylprop-2-en-1-ol, (2R,3R)-2-methyl-2,3-diphenylpent-4-enal, dichlorobis(cyclooctadiene)di-iridium, 5-(dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine, (9R)-Cinchonan-9-amine, Cinchonine Derivative
Aza-Henry (Nitro-Mannich), tert-butyl (phenyl(tosyl)methyl)carbamate, nitroethane, tert-butyl ((1R,2S)-2-nitro-1-phenylpropyl)carbamate, (8α,9R)-9-hydroxy-6′-methoxy-1-(phenylmethyl)-Cinchonanium chloride, Quinine Derivative
Aza-Henry (Nitro-Mannich), tert-butyl (1-tosylpropyl)carbamate, nitromethane, tert-butyl (R)-(1-nitrobutan-2-yl)carbamate, (8α,9R)-9-hydroxy-6′-methoxy-1-(phenylmethyl)-Cinchonanium chloride, Quinine Derivative
Epoxidation, 2-methylenedec-9-enal, hydrogen peroxide, (R)-2-(oct-7-en-1-yl)oxirane-2-carbaldehyde, (8α,9S)-6′-Methoxycinchonan-9-amine with 4-hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin 4-oxide (1:2), Quinine Derivative
Epoxidation, (E)-2-ethylhex-2-enal, hydrogen peroxide, (2R,3S)-2-ethyl-3-propyloxirane-2-carbaldehyde, (8α,9S)-6′-Methoxycinchonan-9-amine with 4-hydroxy-2,6-diphenyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (1:2), Quinine Derivative
Epoxidation, (E)-6-phenylhex-3-en-2-one, hydrogen peroxide, 1-((2S,3R)-3-phenethyloxiran-2-yl)ethan-1-one, (8α,9S)-6′-Methoxycinchonan-9-amine, Quinine Derivative
Aldol reaction, 4-substituted-2,6-heptanediones, 5-substituted-3-methyl-2-cyclohexene-1-ones, (8α,9S)-6′-Methoxycinchonan-9-amine, Quinine Derivative
Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks. Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.