Preparation of cycloalkane-fused dihydropyrimidin-4(3H)-one enantiomers
1998; Elsevier BV; Volume: 9; Issue: 6 Linguagem: Inglês
10.1016/s0957-4166(98)00069-x
ISSN1362-511X
AutoresZsolt Szakonyi, Ferenc Fülöp, G. BERNÁTH, Gabriëlla Török, Antal Péter,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoRacemic 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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