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

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journal contribution
posted on 19.03.2021, 11:34 by Barry M. Trost, Chuanle Zhu, Chloe Christine Ence
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.

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