Synthesis-Stuttgart
(13), 2260-2264
2006
A1
Abstract
The Michael-induced ring closure (MIRC) of amines with 2-bromoalkylidenemalonates has been reinvestigated and the reaction products with primary amines have been identified as (2-iminoethyl)malonates and not 2-aminoalkylidenemalonates as previously reported. The (2-iminoethyl)malonates are formed by ring opening of the intermediate unstable 2-aminocyclopropane-1,1-dicarboxylates (beta-ACCs) and were characterized spectroscopically and via chemical transformation.