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Alkylation, 2,4-disubstituted oxazol-5(4H)-ones, brominated hydrocarbons, 2,4,4-trisubstituted oxazol-5(4H)-ones, (8α,9R)-(8′′α,9′′R)- 1,1′′-[9,10-anthracenediylbis(methylene)]bis[9-hydroxy-Cinchonanium chloride, Cinchonidine Derivative

Alkylation, Alkylation

Bromination, substituted bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid, N-bromosuccinimide, 6-bromo-6,6a-dibutyl-2-oxohexahydro-2H-3,5-methanocyclopenta[b]furan-7-carboxylic acid, gold-catalyst, 1-(2-bromophenyl)-3-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea, Cinchonidine Derivative

Bromination, Lactonization

Desymmetrization, (1R,2S)-cyclohexane-1,2-diol, benzenesulfonyl chloride, (1R,2S)-2-hydroxycyclohexyl benzenesulfonate, 1-methylimidazole, 2-(8α,9S)-cinchonan-9-yl-2,3-dihydro-1H-2,1-Benzazaborol-1-ol, Cinchonidine Derivative

Desymmetrization, Further reactions, Sulfonylation

Atropisomer Synthesis, (E)-10-((([1,1′-biphenyl]-2-carbonyl)oxy)imino)-4,5-dimethylphenanthren-9(10H)-one, aniline, axially chiral biarylnitriles, (8α,9R)-1-[[3,5-bis(1,1-dimethylethyl)phenyl]methyl]-9-hydroxy-cinchonanium bromide, Cinchonidine Derivative

Atropisomer synthesis

Alpha-Alkylation, tert-butyl 2-((diphenylmethylene)amino)acetate, benzyl bromide, tert-butyl (S)-2-((diphenylmethylene)amino)-3-phenylpropanoate, (8α,9R)-(8′′α,9′′R)-(8′′′′α,9′′′′R)-1,1′′,1′′′′-[1,3,5-benzenetriyltris(methylene)]tris[9-(2-propenyloxy)-cinchonanium tribromide, Cinchonidine Derivative

Alkylation, alpha-Alkylation

Racemic resolution, trichostatic acid, R-trichostatic acid, Cinchonidine Base

Racemic resolution, Resolution

Mannich, N-protected phenylmethanimine, acetylacetone, N-protected (S)-3-(amino(phenyl)methyl)pentane-2,4-dione, Cinchonidine Base

Mannich, Mannich

Barbier Reaction, methyl 2,2-dimethyl-3-oxopropanoate, allyl bromide, methyl (R)-3-hydroxy-2,2-dimethylhex-5-enoate, indium, Cinchonidine Base

Barbier Reaction, Further reactions

Atropisomer Synthesis, indole-derived maleimides, methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate, N–N atropisomers, (8α,9R)-10,11-dihydro-6′-(1-methylethoxy)-cinchonan-9-ol, Dihydrocupreine Derivative

Atropisomer synthesis, Michael, Michael Addition

Michael Addition, acetylacetone, (E)-(2-nitrovinyl)benzene, (S)-3-(2-nitro-1-phenylethyl)pentane-2,4-dione, 3-[[(3R,8α,9S)-6′-(2-aminoethoxy)-10,11-dihydrocinchonan-9-yl]amino]-4-[[3,5-bis(trifluoromethyl)phenyl]amino]-3-cyclobutene-1,2-dione, Dihydrocupreine Derivative

Michael, Michael Addition

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