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Synlett 1999; 1999(2): 234-236
DOI: 10.1055/s-1999-2569
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Asymmetric Induction in Stereoselective Carbocyclization of Cyclohexanone Enamines

Eugenius Butkus* , Arvydas Stončius
  • *Department of Organic Chemistry, Vilnius Univesity, Naugarduko 24, 2006 Vilnius, Lithuania; Fax +37 02-63 09 87; E-mail: eugenijus.butkus@chf.vu.lt
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Publication Date:
31 December 1999 (online)

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A highly enantioselective synthesis of bicyclo[3.3.1]nonane diketones 3-5 was accomplished by (S)- and (R)-2-methoxymethylpyrrolidine induced asymmetric cyclization of cyclohexanone enamines 1, 2 in reaction with propenoyl chloride. A possible enantiodifferentiation reaction mechanism was suggested.

enamine cyclization - SMMP/RMMP asymmetric induction - bicyclo[3.3.1][nonanediones

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