Construction of polycyclic frameworks via a DMAP-catalysed tandem addition-(4 + 2) annulation sequence of δ-acetoxy
Chunjie Ni1, Yuejie Yuan, Yuwen Zhang
1College of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Abstract:
Here is reported the DMAP-catalyzed addition/(4 + 2) annulation domino reaction of δ-acetoxy allenoate with either salicylaldehyde-derived oxadiene or pyrrolealdehyde-derived oxadiene, which provides a facile method toward polycyclic frameworks. A cationic intermediate, 3-ammonium-2,4-dienoate, is proposed to be involved via an addition-elimination process between an allenoate and a catalyst, which is capable of undergoing addition with either O- or N-nucleophile and subsequent (4 + 2) annulation with oxadiene.
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