A. Jirgensons et al., The synthesis of 3-amino-3-methylbicyclo[3.3.1]nonanes: Endo-selectivity in the Ritter reaction of 1,3,5,7 alpha-tetramethylbicyclo[3.3.1]nonan-3-ol, J CHEM S P1, (23), 1999, pp. 3527-3530
1,3,5,7 alpha- and 1,3,5,7 beta-Tetramethylbicyclo[3.3.1]nonan-3-ols 3a and
3b were prepared from the corresponding ketones 2a and 2b. 7 alpha-Methyl
isomer 3a gave selectively endo 3 alpha-N-formylaminobicyclononane 10 in th
e Ritter reaction with trimethylsilyl cyanide. 7 beta-Methyl epimer 3b suff
ered water elimination resulting in bicyclo[3.3.1]non-2-ene 12 under the sa
me reaction conditions. The endo-amide structure was confirmed by X-ray ana
lysis..