Azapropellanes 5. Synthesis of chiral (non-racemic) 2-methyl azapropellanes

The preparation of S-(−)-6-methyl-2-piperidinone from S-alanine and R-(−)-5-methyl-2-pyrrolidinone from S-glutamic acid and their conversion into S-2-methyl-1-azoniatricyclo[4.4.4.01,6]tetradecane (2a) and R-2-methyl-1-azoniatricyclo-[4.4.3.01,6]tridecane (2b) with enantiomeric excesses of 95 and 92% respectively are described. The use of these compounds as phase-transfer catalysts did not lead to significant asymmetric induction.