35513-04-3Relevant articles and documents
β-regioselective intermolecular Heck arylation of N,N-disubstituted allylamines
Wu,Marcoux,Davies,Reider
, p. 159 - 162 (2007/10/03)
β-Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary β-aryl allyl amines.
The reaction of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer
Schwan, Adrian L.,Warkentin, John
, p. 1686 - 1694 (2007/10/02)
Tertiary amines bearing two methyl groups and an allylic substituent (X) raect with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding 1-dimethylamino-2-X' maleates, in which X' is the allylic isomer of X.The mechanism postulated involves reversible formation of a zwitterion by attack of the amine at an sp-carbon of DMAD.The zwitterion then undergoes intramolecular allyl transfer, through a 6-membered transition state.Evidence for a zwitterionic intermediate (quaternary ammonium allenolate) includes capture of the allenolate centre by intramolecular addition to a carbonyl group and by proton transfer from chloroform.