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Published September 2, 2016 | Accepted Version
Journal Article Open

Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates


Transition-metal-catalyzed asymmetric allylic alkylation of enolates is a powerful method for the formation of carbon− carbon bonds. Within this field, palladium-catalyzed allylic alkylation reactions have undoubtedly been the most studied. Aside from limited cases, palladium catalysts preferentially form the linear substitution product through alkylation at the less-substituted terminus of the allylic electrophile (Scheme 1). However, in contrast to palladium, most other transition metals (e.g., Mo, W, Fe, Ru, Co, Rh, Ni, Pt, and Ir) have been shown to favor the construction of the branched product, with iridium catalysts being some of the most efficient and selective. The potential application of these chiral, branched products to the synthesis of natural products and biologically active compounds has motivated the development of practical and reliable transition-metal-catalyzed methods for their construction.

Additional Information

© 2016 American Chemical Society. Received: July 6, 2016; Publication Date (Web): August 17, 2016. The authors thank the many past and present co-workers whose efforts have made our contributions in iridium-catalyzed allylic alkylation possible: Prof. Wen-Bo Liu, Dr. Corey M. Reeves, Dr. Scott C. Virgil, Dr. Noriko Okamoto, Eric J. Alexy, Dr. Allen Y. Hong, and Dr. Kristy Tran. Support for our program has been made available from the NIH-NIGMS (R01GM080269) and Caltech. Additionally, J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program in Environmental Chemistry, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). The authors declare no competing financial interest.

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August 20, 2023
October 20, 2023