Reactions - Buchler GmbH

Racemic resolution, racemic QUINAPs, (R)-QUINAPs, (8α,9R)-9-hydroxy-1-(phenylmethyl)-Cinchonanium chloride, Cinchonidine Derivative

Atropisomer synthesis, Racemic resolution, Resolution

Addition, 4‐nitro‐5‐styrylisoxazoles, nitromethane, 5-(3-nitro-2-phenylpropyl)isoxazoles, N-[3,5-bis(trifluoromethyl)benzyl]-cinchonidinium Bromide, Cinchonidine Derivative

Cyclization, substituted 2-(2-(benzylideneamino)phenyl)malonate, functionalized indolines, (8α,9R)-9-hydroxy-1-(phenylmethyl)-Cinchonanium chloride, Cinchonidine Derivative

Cyclization, Cyclization, Further Cyclizations

Sulfonimidate formation, N-(p-tolylthio)benzamide, phenylmethanol, sulfinimidate esters, 3-[[[3,5-Bis(trifluoromethyl)phenyl]methyl]amino]-4- [[(8α,9S)-6′-methoxycinchonan-9-yl]amino]- 3-Cyclobutene-1,2-dione, Quinine Derivative

Further reactions, Sulfonimidate formation

Thiolation, 1-(9H-carbazol-9-yl)prop-2-en-1-one, potassium benzothioate, ethyl 2-bromo-2-methylpropanoate, ethyl 4-(benzoylthio)-5-(9H-carbazol-9-yl)-2,2-dimethyl-5-oxopentanoate, copper catalyst, (E)-2-((2,6-diisopropylphenyl)imino)-2-(2-isopropylphenyl)-N-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)acetamide, Quinine Derivative

Further reactions, Thiolation

Michael Addition, 3-hydroxy-4H-chromen-4-one, 1H-inden-1-one, (S)-3-hydroxy-2-(3-oxo-2,3-dihydro-1H-inden-1-yl)-4H-chromen-4-one, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione, Quinine Derivative

Michael, Michael Addition

Amination, boron heterocycle, benzenesulfonimidamide, 1,5‐heteroatom (sulfur/boron) stereogenic architectures, (8α,9R)-1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-hydroxy-6′-methoxy-cinchonanium bromide, Quinine Derivative

Atropisomer Synthesis, bromonitroalkenes, naphthalen-2-ol, (Z)-2-(2-bromo-2-nitrovinyl)-1-(2-methoxyphenyl)naphthalene, (1R,2R)-1-((S)-1-(2-methoxyphenyl)naphthalen-2-yl)-2-nitro-1,2-dihydronaphtho[2,1-b]furan, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-6′-methoxycinchonan-9-yl]amino]-3-Cyclobutene-1,2-dione, Quinine Derivative

Atropisomer synthesis, Kinetic resolution, Resolution

Mannich reaction, substituted benzo[d]thiazol-2-amine, malonates, 2-((benzo[d]thiazol-2-ylamino)methyl)malonates, N-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N′-[(8α,9S)-6′-methoxycinchonan-9-yl]-thiourea, Quinine Derivative

Mannich, Mannich

Strecker Reaction, α-amido sulfones, cyanohydrins, N-protected (S)-2-amino-3,3-dimethylbutanenitrile, 9-hydroxy-6′-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]-cinchonanium bromide, Quinine Derivative

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