New synthetic methods for spirolactams bearing an α-methylene-γ-butyrolactone or its analogous methylene-lactam have been developed. The allylation of γ-phenylthio-functionalized γ-lactams with 2-(acetoxy)methyl acrylamides was accomplished by using 2.5 equivalents of NaH to give the corresponding adducts in excellent yields. The remaining phenylthio group was substituted with a hydroxy group by treatment with CuBr, and the resulting γ-hydroxyamides were cyclized under acidic conditions to afford the corresponding methylene-lactam-fused spirolactams in high yields. On the other hand, methylene-lactone-fused spirolactams could be delivered from the allyl adducts in high yields through a sequential N-Boc protection/desulfinative lactonization.

中文翻译：

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通过γ-苯硫基官能化的γ-内酰胺的亲电酰胺烯丙基化分叉合成亚甲基内酯和亚甲基内酰胺融合的螺内酰胺

已经开发出用于合成带有α-亚甲基-γ-丁内酯或其类似物亚甲基-内酰胺的螺内酰胺的新方法。γ-苯硫基官能化的γ-内酰胺与2-（乙酰氧基）甲基丙烯酰胺的烯丙基化是通过使用2.5当量的NaH以优异的产率得到相应的加合物来实现的。通过用CuBr处理，将剩余的苯硫基基团用羟基取代，并且将所得的γ-羟基酰胺在酸性条件下环化，以高产率提供相应的亚甲基-内酰胺基融合的螺内酰胺。另一方面，可以通过顺序的N -Boc保护/脱硫内酯化从烯丙基加合物以高收率递送亚甲基-内酯融合的螺内酰胺。