Intermolecular Stereoselective Iridium-Catalyzed Allylic Alkylation: An Evolutionary Account
Our lab has long been interested in the development of methods for the creation of enantioenriched all-carbon quaternary stereocenters. Historically, our interest has centered on palladium-catalyzed allylic alkylation, though recent efforts have moved to include the study of iridium catalysts. Whereas palladium catalysts enable the preparation of isolated stereocenters, the use of iridium catalysts allows for the direct construction of vicinal stereocenters via an enantio-, diastereo-, and regioselective allylic alkylation. This Account details the evolution of our research program from inception, which focused on the first iridium-catalyzed allylic alkylation to prepare stereodyads containing a single quaternary stereocenter, to our most recent discovery that allows for the synthesis of vicinal quaternary centers.
Additional Information© 2018 Georg Thieme Verlag Stuttgart. Received: 28.05.2018; Accepted after revision: 25.06.2018; Published online: 15.08.2018. 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 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.
Published - s-0037-1610217.pdf
Accepted Version - nihms-1015480.pdf