Divergent Iron-Catalyzed Olefin Cyclization for Saturated N-Heterocycles Syntheses

Area of Science:

• Organic Chemistry
• Catalysis
• Medicinal Chemistry

Background:

• Saturated N-heterocycles are crucial building blocks in pharmaceuticals, agrochemicals, and materials science.
• Existing catalytic methods often yield only one specific N-heterocycle from a given precursor.
• Achieving regio-complementary cyclization to access distinct N-heterocyclic motifs from a common starting material remains a significant challenge.

Purpose of the Study:

• To develop novel catalytic protocols for the synthesis of diverse saturated N-heterocycles.
• To enable divergent cyclization of a common precursor into multiple, distinct N-heterocyclic structures.
• To establish simple and efficient iron-catalyzed methods for accessing valuable heterocyclic scaffolds.

Main Methods:

• Development of two distinct iron catalytic systems.
• Utilizing a common N-containing substrate for cyclization reactions.
• Optimization of reaction conditions to control regioselectivity and achieve divergent synthesis.

Main Results:

• Successful synthesis of pyrrolidines, piperidines, and azepanes from a single precursor.
• Demonstration of divergent cyclization pathways controlled by the developed iron catalysts.
• Establishment of simple and efficient protocols with high yields and selectivity.

Conclusions:

• The developed iron catalytic protocols offer a versatile approach for synthesizing a range of saturated N-heterocycles.
• These methods overcome the limitations of traditional approaches by enabling divergent synthesis from a common precursor.
• The findings provide valuable tools for medicinal chemistry, agrochemistry, and materials science, facilitating access to diverse heterocyclic compounds.