Chemistry of bridged lactams and related heterocycles

Michal Szostak, Jeffrey Aubé

Research output: Contribution to journalReview articlepeer-review

183 Scopus citations

Abstract

The article presents the general structures of bridged lactams and their derivatives that will be reviewed. The synthesis of bridged lactams with the N-(CO) bond placed on a bridge having two or more carbons is challenging because of the strain associated with distorted amide bonds and general lack of stabilizing features on the lactam skeleton. In some cases, the high reactivity of nonplanar amide bonds may be incompatible with the reaction conditions used for their synthesis. In this section, bridged lactams are classified on the basis of the reaction type employed for their preparation. Condensation reactions that directly form the amide bond can be used to prepare this type of lactams. However, alternative approaches with the amide bond already present in the precursor usually lead to more strained and diverse examples.

Original languageEnglish (US)
Pages (from-to)5701-5765
Number of pages65
JournalChemical Reviews
Volume113
Issue number8
DOIs
StatePublished - Aug 14 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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