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A Highly Stereoselective Diels–Alder Cycloaddition of Enones with Chiral Cyclic 2‑Amidodienes Derived from Allenamides

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posted on 20.09.2013, 00:00 by Li-Chao Fang, Richard P. Hsung, Zhi-Xiong Ma, William R. Presser
Lewis acid promoted Diels–Alder cycloadditions of a series of de novo chiral cyclic 2-amidodienes are described. These cyclic 2-amidodienes are derived from chiral α-allyl allenamides via a sequence of E-selective 1,3-H shift and 6π-electron pericyclic ring closure. With enones serving as effective dienophiles, these cycloadditions can be highly diastereoselective depending upon the chiral amide substituent, thereby representing a facile entry to optically enriched [2.2.2]bicyclic manifolds.