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This study introduces a novel lactam downsizing strategy using removable directing groups and rhodium-catalyzed carbon-carbon activation. This method efficiently synthesizes smaller lactam rings from larger precursors, offering broad applicability in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Catalysis

Background:

  • Ring-contraction reactions are crucial for synthesizing strained or less accessible cyclic compounds.
  • Existing methods for lactam ring contraction are limited in scope and efficiency.
  • Developing new strategies for accessing smaller lactam rings is of significant synthetic interest.

Purpose of the Study:

  • To develop an unprecedented lactam downsizing strategy.
  • To utilize removable directing groups (DGs) and rhodium-catalyzed C-C activation for ring contraction.
  • To establish an efficient method for installing and removing DGs in lactam synthesis.

Main Methods:

  • Installation of directing groups onto lactam substrates using silylated amines and titanium catalysts.
  • Rhodium-catalyzed C-C activation for ring contraction.
  • Acid-mediated hydrolysis for removal of the directing group and regeneration of the lactam.

Main Results:

  • Demonstrated a broad substrate scope and excellent functional group tolerance for the ring-contraction reaction.
  • Achieved high selectivity for the formation of gamma-lactams, enabling "6-to-5", "7-to-5", and "8-to-5" ring contractions.
  • Obtained preliminary results for selective "7-to-6" ring contraction by optimizing DGs and ligands.
  • Density functional theory (DFT) calculations elucidated the origin of product selectivity.

Conclusions:

  • The developed method provides an efficient and versatile route for lactam ring contraction.
  • The strategy allows access to smaller lactam rings from readily available larger precursors.
  • This work expands the synthetic toolbox for constructing diverse lactam structures.