Synthesis of Polysubstituted Ferrocenesulfoxides.

Area of Science:

• Organometallic Chemistry
• Synthetic Organic Chemistry
• Chiral Compound Synthesis

Background:

• Ferrocenesulfoxides are valuable chiral building blocks in organic synthesis.
• Accessing highly substituted and enantiopure ferrocene derivatives remains a synthetic challenge.

Purpose of the Study:

• To develop synthetic methodologies for polysubstituted ferrocenesulfoxides.
• To utilize directed deprotometalation with polar organometallic reagents.
• To synthesize novel enantiopure di-, tri-, and tetrasubstituted ferrocenesulfoxides.

Main Methods:

• Directed deprotometalation of enantiopure 2-substituted tert-butylferrocenesulfoxides.
• Introduction of a third substituent at the 5-position.
• Selective removal of the trimethylsilyl group to access unique derivatives.

Main Results:

• Successful synthesis of various 2,5-disubstituted ferrocenesulfoxides.
• Generation of new enantiopure di-, tri-, and tetrasubstituted ferrocenesulfoxides.
• Unexpected outcomes in 'halogen dance' reactions rationalized by pKa calculations.

Conclusions:

• Established efficient synthetic routes to diverse polysubstituted ferrocenesulfoxides.
• Demonstrated the utility of directed deprotometalation for creating complex chiral ferrocenes.
• Expanded the scope of accessible enantiopure ferrocene derivatives.