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Synthesis 1993; 1993(7): 725-728
DOI: 10.1055/s-1993-25929
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Enantioselective Synthesis of 2-Alkyl-2-cyanocycloalkanones with a Quaternary Stereogenic Center

Dieter Enders* , Andrea Zamponi, Gerhard Raabe, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany
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Publication Date:
17 September 2002 (online)

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2-Alkyl-2-cyanocycloalkanones 4 bearing a quaternary stereogenic center are synthesized in good overall yields and high enantiomeric excesses (ee = 90-95%) employing the SAMP-/RAMP-hydrazone method. The absolute configuration is confirmed by NMR-spectroscopic investigations on SAMP-hydrazone 3a and an X-ray structure analysis of SAMP-hydrazone 3f.