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O-Alkylation, C/O-substituted 2′-hydroxy-3,4-dihydro-[1,1′-binaphthalen]-2(1H)-one, benzyl iodide, atropisomeric biaryls, (9S)-9-hydroxy-6′-methoxy-1-[(2,3,4-trifluorophenyl)methyl]-cinchonanium bromide, Quinidine Derivative

Alkylation, Alkylation, Atropisomer synthesis

Oxa-Michael, (E)-5-(4-hydroxyphenyl)-1-(p-tolyl)pent-2-en-1-one, Iodobenzene diacetate, (S)-2-(2-oxo-2-(p-tolyl)ethyl)-1-oxaspiro[4.5]deca-6,9-dien-8-one, 3-[[(9R)-6′-methoxycinchonan-9-yl]amino]-4-[[(1R)-1-phenylethyl]amino]-3-cyclobutene-1,2-dione, Quinidine Derivative

Cyclization, Dearomatization, Further Cyclizations, Further reactions, Intramolecular cyclization, Michael Addition, Oxa-Michael Addition, Spirocyclization

Oxa-Michael, (E)-6-hydroxy-1-phenylhex-2-en-1-one, (R)-1-phenyl-2-(tetrahydrofuran-2-yl)ethan-1-one, N-[3,5-bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxycinchonan-9-yl]-urea, Quinidine Derivative

Cyclization, Further Cyclizations, Intramolecular cyclization, Michael Addition, Oxa-Michael Addition

Aldol reaction, methyl 2-fluoro-3-((4-methoxyphenyl)thio)-3-oxopropanoate, 4-bromobenzaldehyde, S-(4-methoxyphenyl) (2S,3S)-3-(4-bromophenyl)-2-fluoro-3-hydroxypropanethioate, N-[3,5-bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxycinchonan-9-yl]-urea, Quinidine Derivative

Aldol, Aldol

Bromolactonization, 4-phenylpent-4-enoic acid, N-bromosuccinimide, (R)-5-(bromomethyl)-5-phenyldihydrofuran-2(3H)-one, N-[(8α,9S)-6′-(2,2-Dimethylpropoxy)-2′-phenylcinchonan-9-yl]-2,3,4-trimethoxybenamide, Cupreine Derivative

Bromination, Cyclization, Lactonization

Cyclization – Aziridination – Nuclephilic Addition, ethyl 2-azidoacrylate, 3-methoxybenzenethiol, ethyl (R)-2-((3-methoxyphenyl)thio)aziridine-2-carboxylate, N-(8α,9S)-Cinchonan-9-yl-8-quinolinesulfonamide, Cinchonidine Derivative

Aziridination, Cyclization, Further reactions, Nucleophilic Addition

alpha-Fluorination, acid chlorides, N-fluorbenzolsulfonimid, methanol, methyl (R)-2-fluoro-2-(4-methoxyphenyl)acetate, Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel, 6′-methoxy-(9S)-Cinchonan-9-ol-9-benzoate, Quinidine Derivative

alpha-Fluorination, Fluorination

[8+3]-Cycloaddition, 2-(2-oxopropyl)cyclopropane-1,1-dicarbonitrile, Tropone, (R)-2-(2-oxopropyl)-2,3-dihydrocyclohepta[b]pyran-4,4(9H)-dicarbonitrile, N-[3,5-Bis(trifluoromethyl)phenyl]-N′-(8α,9S)-cinchonan-9-ylthiourea, Cinchonidine Derivative

[8+3]-Cycloaddition, Cycloaddition

Mannich reaction, ketones, ethyl (E)-2-((4-methoxyphenyl)imino)acetate, 3,3,4-trisubstituted ethyl (R)-2-((4-methoxyphenyl)amino)-4-oxobutanoate, (R)-pyrrolidine-3-carboxylic acid, N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxycinchonan-9-yl]thiourea, Quinidine Derivative

Mannich, Mannich

Cyanation, beta-trifluoromethylated chalcones, 2-hydroxy-2-methylpropanenitrile, (R)-4-oxo-2,4-diphenyl-2-(trifluoromethyl)butanenitrile, (9S)-1-[[2,5-bis(trifluoromethyl)phenyl]methyl]-6′,9-dimethoxy-cinchonanium bromide, Quinidine Derivative

Cyanation, Michael, Michael Addition

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