Synthesis of Fluoroalkyl Cyclopentenes: Highly Diastereoselective Phosphine-Catalyzed [3+2] Annulation of β-Fluoroalkylvinyl Arylsulfones with Morita-Baylis-Hillman Carbonates

A phosphine-catalyzed [3+2] annulation of beta-fluoroalkylvinyl arylsulfones and Morita-Baylis-Hillman carbonates was achieved to generate tetrasubstituted cyclopentene carboxylates with a fluoroalkylated stereogenic center at C4. The substrates with various substituents provided the expected [3+2] products in generally excellent yields and diastereoselectivities. This transformation provides a simple and efficient method for the synthesis of fluoroalkyl-substituted cyclopentene compounds.

Automated summary

A phosphine-catalyzed reaction successfully generated fluoroalkyl-substituted cyclopentene carboxylates with four substituents, including a fluoroalkyl stereogenic center at C4. Substrates with different substituents provided excellent yields and diastereoselectivities. This transformation offers a simple and efficient method for synthesizing fluoroalkyl-substituted cyclopentene compounds.