Chiral discrimination processes by C9 carbamate derivatives of dihydroquinine: interaction mechanisms of diastereoisomeric 9-O-[(S)- or (R)-1-(1-naphthyl)ethylcarbamate]dihydroquinine and the two enantiomers of N-(3,5-dinitrobenzoyl)alanine methyl ester

Computational and NMR investigations of diastereoisomeric aggregates arising from the interaction of 9-O-[(S)- or (R)-1-(1-naphthyl)ethylcarbamate]dihydroquinine and the two enantiomers of N-(3,5-dinitrobenzoyl)alanine methyl ester pointed out the origin of chiral discrimination phenomena occurring in CDCl3 solutions.

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9-O-[(S)-1-(1-Naphthyl)ethylcarbamate]dihydroquinineC33H37N3O3[α]D25=-6.8 (c 1, CHCl3)Source of chirality: quinine and (S)-(+)-1-(1-naphthyl)ethyl isocyanateAbsolute configuration: (S)

9-O-[(R)-1-(1-Naphthyl)ethylcarbamate]dihydroquinineC33H37N3O3[α]D25=+16.05 (c 1, CHCl3)Source of chirality: quinine and (R)-(−)-1-(1-naphthyl)ethyl isocyanateAbsolute configuration: (R)