Preparation of cycloalkane-fused dihydropyrimidin-4(3H)-one enantiomers

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Abstract

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.

Original languageEnglish
Pages (from-to)993-999
Number of pages7
JournalTetrahedron Asymmetry
Volume9
Issue number6
DOIs
Publication statusPublished - Mar 27 1998

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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