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Aminohydroxylation, enones, tert-butyl (tosyloxy)carbamate, 4,5-disubstituted oxazolidinones, (8α,9S)-6′-Methoxycinchonan-9-amine, Quinine Derivative

Aminohydroxylation, Further reactions

Epoxidation, 2‐Methylnaphthoquinone, sodium hypochlorite, (1aR,7aS)-1a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione, 1-(9-anthracenylmethyl)-10,11-dihydro-6′,9-dihydroxy-(9S)-cinchonanium chloride, Dihydrocupreidine Derivative

Epoxidation

Jorgensen`s oxaziridination, substituted (E)-N-tosylformimidoyl, meta-chloroperoxybenzoic acid, (3S)-substituted 2-tosyl-1,2-oxaziridine, (9S)-9-(9-anthracenylmethoxy)-10,11-dihydro-cinchonan-6′-ol, Dihydrocupreidine Derivative

Further reactions, Oxaziridination

Epoxidation, 2-methylnaphthalene-1,4-dione, sodium hypochlorite, (1aS,7aR)-1a-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione, 1-(9-anthracenylmethyl)-10,11-dihydro-6′,9-dihydroxy-(9S)-cinchonanium chloride, Dihydrocupreidine Derivative

Epoxidation

Fluorination, α,β-unsaturated aldehydes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide, (2R),4-disubstituted (E)-2-fluoro but-3-enal, (9R)-9-Aminocinchonan-6′-ol, Cupreidine Derivative

alpha-Fluorination, Fluorination

Michael Addition, tert-butyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate, acrylaldehyde, chiral aldehydes, (9S)-9-(9-Phenanthrenyloxy)cinchonan-6′-ol, Cupreidine Derivative

Michael, Michael Addition

Michael Addition, cyclohex-2-en-1-one, 2-methyl-2-(2-nitroethyl)cyclopentane-1,3-dione, 3-nitrobenzoic acid, boron trifluoride etherate, (3aR,5R,5aS,9aR,9bR)-9b-hydroxy-3a-methyl-5-nitrodecahydro-3H-cyclopenta[a]naphthalene-3,9(3aH)-dione, (8α,9S)-6′-Methoxycinchonan-9-amine, Quinine Derivative

Michael, Michael Addition

Bromoamination, allylic alcohol, N,N-Dibromo-4-nitrobenzenesulfonamide, tert-butylchlorodimethylsilane, bromoamine, N-[(8α,9S)-6′-Methoxycinchonan-9-yl]-N′-[4-(triphenylmethyl)phenyl]thiourea, Quinine Derivative

Amination, Bromination

γ-Alkylation, α-branched enals, bis(4-(dimethylamino)phenyl)methanol, substituted 5,5-bis(4-(dimethylamino)phenyl)pent-2-enal, (9R)-9-Aminocinchonan-6′-ol, Cupreidine Derivative

Alkylation, Alkylation

Cascade reaction, cinnamic thioesters, acetylacetone, 3,4-dihydropyran-2-ones, (8α,9R)-9-hydroxy-6′-methoxy-1-(phenylmethyl)-Cinchonanium bromide, Quinine Derivative

Cascade reaction, Cyclization

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