Enantioselective hantzsch dihydropyridine synthesis via metalated chiral alkyl acetoacetate hydrazones1
1988; Elsevier BV; Volume: 29; Issue: 49 Linguagem: Inglês
10.1016/s0040-4039(00)82366-7
ISSN1873-3581
AutoresDieter Enders, Stephan F. Müller, Ayhan S. Demir,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAn efficient, overall enantioselective variant of the Hantzsch synthesis of 4-aryl-1,4-dihydropyridines 5 (ee = 84 - 98%), important biologically active compounds (e. g. as calcium channel blockers), is described. Key step of the new procedure is the asymmetric Michael addition of metalated chiral alkyl acetoacetate hydrazones (S)-2 to the Knoevenagel acceptors 4. An accurate method to determine the enantiomeric excess of chiral dihydropyridines is also reported.
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