Enzymatic Resolution and Decarboxylative Functionalization of α-Sulfinyl Esters.

Area of Science:

• Organic Chemistry
• Enzymatic Synthesis
• Medicinal Chemistry

Background:

• α-Sulfinyl esters are versatile synthetic intermediates.
• Efficient methods for their preparation and functionalization are crucial for developing new therapeutics.

Purpose of the Study:

• To develop a robust method for preparing enantiomerically enriched α-sulfinyl esters.
• To explore the subsequent functionalization of these compounds.
• To apply the developed method in the asymmetric synthesis of a 15-prostaglandin dehydrogenase inhibitor.

Main Methods:

• Preparation of α-sulfinyl esters via thiol substitution and oxidation.
• Enzymatic resolution using lipoprotein lipase.
• Decarboxylative halogenation, dihalogenation, and trihalogenation reactions.
• Palladium-catalyzed cross-coupling reactions.
• Asymmetric synthesis of a 15-prostaglandin dehydrogenase inhibitor.

Main Results:

• High yields and enantiomeric ratios achieved during enzymatic resolution.
• Successful synthesis of various functionalized sulfoxides.
• Demonstrated application in the asymmetric synthesis of a biologically active compound.

Conclusions:

• The developed methodology provides efficient access to enantiomerically enriched functionalized sulfoxides.
• This approach is valuable for the asymmetric synthesis of complex molecules, including pharmaceutical agents.