An efficient one-pot synthesis of functionalized azamacrocycles from methyl 2-siloxy-2-vinylcyclopropanecarboxylates

The (N)-benzylamine substituted 2-siloxy-2-vinylcyclopropanecarboxylates 5, 7, 9, 10, 13, 15, and 17 upon desilylation-ring opening induced by cesium fluoride and subsequent intramolecular Michael addition-ring closure, affor d azamacrocycles 18-22 and 24-26 in moderate to good yields in a one-pot op eration. The aromatic spacer in amine precursor 12 does not allow formation of ring 23 due to ring strain. Except in the case of 5, dimers or higher o ligomers are not observed.