Tetrahedron Asymmetry p. 993 - 999 (1998)
Update date:2022-08-03
Topics: Characterization Melting point Reagents HPLC Hydrolysis Enantiomers Derivatization Absolute configuration determination Optical rotation Deprotection Purification Protection and Functionalization Chiral resolution or asymmetric synthesis
Szakonyi, Zsolt
Fueloep, Ferenc
Bernath, Gabor
Toeroek, Gabriella
Peter, Antal
Racemic cis-2-amino-1-cyclopentane- or -cyclohexane-1-carboxylic acid was reacted with (R)-α-methylbenzylamine to form homochiral amides 3, 4 and 8, 9. The ring closures of 3, 4 and 8, 9 with aryl imidates resulted in cyclopentane cis-fused and cyclohexane cis- and trans-fused dihydropyrimidin- 4-one enantiomers with loss of the N-substituent. The absolute configurations were determined by hydrolysis of 5, 6 and 10-13 to the corresponding amino acids.
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