4.8 Article

Cation-π control of regiochemistry of intramolecular Schmidt reactions en route to bridged bicyclic lactams

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 10, 页码 2766-+

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AMER CHEMICAL SOC
DOI: 10.1021/ja068919r

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  1. NIGMS NIH HHS [R01 GM049093-14, R01 GM049093-15, R01 GM049093-13, GM-49093, R01 GM049093] Funding Source: Medline

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The regiochemistry of the intramolecular Schmidt reaction of 2-substituted ketones has proved susceptible to control by the placement of an aromatic group at an adjacent position, permitting the selective formation of a series of bridged bicyclic lactams from these substrates. This phenomenon is ascribed to the presence of stabilizing through-space interactions between the positively charged leaving group and the aromatic substituents in a key azidohydrin intermediate.

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