Abstract
On treatment with t-BuLi in presence of HMPA, methoxybenzamides, e.g. I (Ar = Ph, 4-MeOC6H4), cyclized with dearomatization to give Me dienyl ethers, e.g. II, which were hydrolyzed with dil. HCl to give single stereo- and regioisomers of pyrrolidine-fused cyclohexenones, e.g. III. The bicyclic enones are versatile synthetic intermediates which undergo transformations such as stereoselective redn. and conjugate addn., regioselective Baeyer-Villiger oxidn., bromination and hydrogenation. [on SciFinder (R)]
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