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Trans-selective cyclizations of alpha-bromocarboxamides and E/Z-mixed internal olefins catalyzed by a Fe salt.

There are several reports of lactam cyclizations, but most yield less-substituted lactam rings. Therefore, diastereoselective cyclization to yield highly substituted lactams is one of the challenges in this field. We… Click to show full abstract

There are several reports of lactam cyclizations, but most yield less-substituted lactam rings. Therefore, diastereoselective cyclization to yield highly substituted lactams is one of the challenges in this field. We therefore propose a strategy involving the reactions of α-halocarboxamides with E/Z-mixed internal olefins here. An Fe/triphos catalyst system is effective in reactions between α-bromocarboxamides and internal olefins to form trans lactams with quaternary carbons. Control experiments reveal that the reaction involves a radical process. This reaction may be useful in the field of pharmaceuticals, as γ-lactam moieties constitute the core structures of numerous drugs and natural alkaloids.

Keywords: selective cyclizations; alpha bromocarboxamides; internal olefins; trans selective; mixed internal; cyclizations alpha

Journal Title: Chemical communications
Year Published: 2022

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