Determination of the relative configuration of tropinone and granatanone aldols by using TBDMS ethers

• Ryszard Lazny,
• Aneta Nodzewska,
• Katarzyna Sidorowicz and
• Przemyslaw Kalicki

Beilstein J. Org. Chem. 2012, 8, 1877–1883, doi:10.3762/bjoc.8.216

• relative configurations of tert-butyldimethylsilyl (TBDMS) ethers of all four diastereomers of the aldols of tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one), as well as of granatanone (9-methyl-9-azabicyclo[3.3.1]nonan-3-one), were determined from NMR data, and from the observed interconversion of the

• isomerization; granatanone; stereoselective reaction; tropinone; Introduction Enantiomerically pure, and racemic, diastereomerically pure aldols of tropinone have been used as key intermediates in stereoselective syntheses of natural tropane alkaloids and their analogues [1], including the unnatural enantiomer

• and enantiomerically pure aldols of tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one) and granatanone (9-methyl-9-azabicyclo[3.3.1]nonan-3-one) (Figure 1) were synthesized by enantioselective deprotonation with lithium amide bases followed by diastereoselective aldol reaction with aldehydes [10][11