Stereoselective polar radical crossover for the functionalization of strained-ring systems

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Small ring systems are crucial in drug discovery.
• Efficient synthesis of functionalized small rings is challenging.
• Radical-polar crossover of organoborates enables simultaneous C-C bond formation.

Purpose of the Study:

• To develop a step-economic, one-pot strategy for synthesizing substituted small rings.
• To leverage polar radical crossover for stereoselective functionalization.
• To access tri-substituted azetidines, cyclobutanes, and five-membered heterocycles.

Main Methods:

• One-pot preparation of strained organoboron species.
• Application of polar radical crossover of borate derivatives.
• Stereoselective synthesis of cyclic compounds.

Main Results:

• Successful stereoselective synthesis of tri-substituted azetidines.
• Efficient access to cyclobutanes and five-membered carbo- and heterocycles.
• Demonstration of a versatile one-pot strategy.

Conclusions:

• The presented method offers a powerful and efficient route to valuable small ring motifs.
• This strategy addresses the scarcity of step-economic methods for small ring functionalization.
• The approach merges organoboron chemistry with polar radical chemistry for novel synthetic outcomes.