European Journal of Organic Chemistry p. 3249 - 3256 (2010)
Update date:2022-09-26
Topics:
Santos, Bruna S.
Cardoso, Ana L.
Beja, Ana Matos
Silva, Manuela Ramos
Paixao, Jose A.
Palacios, Francisco
Pinho E Melo, Teresa M. V. D.
The reactivity of allenic esters towards activated N-sulfonylimines in the presence of DABCO was explored. A formal [2+2] cycloaddition of benzyl buta- -dienoate and N-aryl idenebenzenesulfonamides yielded mainly 2-methyleneazet-idines. Interestingly, a DABCO-catalysed reaction of allenoates, bearing a chiral auxiliary on the ester moiety, with N- arylidenebenzenesulfonamides led to optically active aza-Baylis-Hillman products and 2-azetine derivatives.
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