An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich Reaction

Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n = 2-5) to be obtained in good yields.

Mityuk A. P.; Denisenko A. V.; Dacenko O. P.; Grygorenko O. O.; Mykhailiuk P. K.; Volochnyuk D. M.; Shishkin O. V.; Tolmachev A. A.
Synthesis 2010, 03, 493-497
DOI: 10.1055/s-0029-1217137