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Published September 21, 2018 | Supplemental Material + Accepted Version
Journal Article Open

Palladium-Catalyzed Enantioselective C_(sp)^3–C_(sp)^3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks


A general method for the enantioselective synthesis of carbo- and heterocyclic carbonyl compounds bearing fluorinated α-tetrasubstituted stereocenters using palladium-catalyzed decarboxylative allylic alkylation is described. The stereoselective C_(sp)^3–C_(sp)^3 cross-coupling reaction delivers five- and six-membered ketone and lactam products bearing (poly)fluorinated tetrasubstituted chiral centers in high yields and enantioselectivities. These fluorinated, stereochemically rich building blocks hold potential value in medicinal chemistry and are prepared using an orthogonal and enantioselective approach into such chiral moieties compared to traditional approaches, often without the use of electrophilic fluorinating reagents.

Additional Information

© 2018 American Chemical Society. Received: July 26, 2018; Published: September 5, 2018. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. E.L.G. recognizes the NSF for a predoctoral research fellowship (No. DGE-1745301). Y.L. thanks the Program of Leading Graduate Schools: IGER Program in Green Natural Sciences (MEXT) at Nagoya University for financial support. The authors declare no competing financial interest.

Attached Files

Accepted Version - nihms-989121.pdf

Supplemental Material - ol8b02369_si_001.pdf


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