Pd-Catalyzed Regio-, Diastereo-, and Enantioselective [3+2] Cycloaddition Reactions: Access to Chiral Cyclopentyl Sulfones

The palladium-catalyzed [3 + 2] cycloaddition using in situ generated sulfone-TMM species to construct various chiral cyclopentyl sulfones in a highly regio-, diastereo- (dr >15:1), and enantioselective (up to 99% ee) manner is reported. The present strategy can tolerate different types of sulfone-TMM donors and acceptors, and enables the construction of three chiral centers in a single step, specifically with a chiral center bearing the sulfone moiety. The robust chiral diamidophosphite ligand is the key to the reactivity and selectivities of this transformation.

Automated summary

This study reports a palladium-catalyzed [3 + 2] cycloaddition using in situ generated sulfone-TMM species to construct various chiral cyclopentyl sulfones in a highly regio-, diastereo-, and enantioselective manner. The robust chiral diamidophosphite ligand is crucial for the reactivity and selectivities of this transformation, allowing for the construction of three chiral centers in a single step.