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Published August 5, 2015 | Accepted Version + Supplemental Material
Journal Article Open

Synthesis and exploration of electronically modified (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX in palladium-catalyzed enantio- and diastereoselective allylic alkylation: a practical alternative to (R)-(p-CF₃)₃-t-BuPHOX


The synthesis of the novel electronically modified phosphinooxazoline (PHOX) ligand, (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX, is described. The utility of this PHOX ligand is explored in both enantio- and diastereoselective palladium-catalyzed allylic alkylations. These investigations prove (R)-5,5-dimethyl-(p-CF₃)₃-i-PrPHOX to be an effective and cost-efficient alternative to electronically modified PHOX ligands derived from the prohibitively expensive (R)-t-leucine.

Additional Information

© 2015 Elsevier Ltd. Received 27 May 2015, Accepted 10 June 2015, Available online 17 June 2015. The authors wish to thank the NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. R.A.C. gratefully acknowledges the support of this work provided by a fellowship from the National Cancer Institute of the National Institutes of Health under Award Number F31A17435.

Attached Files

Accepted Version - nihms705028.pdf

Supplemental Material - mmc1.pdf


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