Construction of Tertiary Chiral Centers by Pd-catalyzed Asymmetric Allylic Alkylation of Prochiral Enolate Equivalents
The palladium-catalyzed decarboxylative allylic alkylation of enol carbonates derived from lactams and ketones is described. Employing these substrates with an electronically tuned Pd catalyst system trisubstituted chiral centers are produced. These stereocenters have been previously challenging to achieve using Pd complex/chiral P–N ligand systems.
Additional Information© 2015 Elsevier B.V. Received Date: 2 April 2015; Revised Date: 19 May 2015; Accepted Date: 25 May 2015; Available online 29 May 2015. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. Y.K. expresses his special thanks to the International Engineering Science Consortium for financial support. Y.N. thanks Toray Industries Inc. for a postdoctoral fellowship. N.O. is grateful for a postdoctoral fellowship provided by Hiroshima International University. The authors thank Scott Virgil (Caltech) for instrumentation assistance and Dr. Douglas C. Behenna (Caltech) for initial experimental results.
Accepted Version - nihms695724.pdf
Supplemental Material - mmc1.pdf