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Published September 11, 2017 | Supplemental Material + Accepted Version
Journal Article Open

Enantioselective Synthesis of Acyclic α-Quaternary Carboxylic Acid Derivatives through Iridium-Catalyzed Allylic Alkylation


The first highly enantioselective iridium-catalyzed allylic alkylation providing access to products bearing an allylic all-carbon quaternary stereogenic center has been developed. The reaction utilizes a masked acyl cyanide (MAC) reagent, which enables the one-pot preparation of α-quaternary carboxylic acids, esters, and amides with a high degree of enantioselectivity. The utility of these products is further explored via a series of diverse product transformations.

Additional Information

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: July 10, 2017; Accepted manuscript online: July 19, 2017; Version of record online: August 9, 2017. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. J.C.H. thanks the Camille and Henry Dreyfus postdoctoral program, and S.E.S. thanks the NIH-NIGMS for a predoctoral fellowship (F31GM120804). Dr. Michael Takase, Dr. Lawrence Henling, and Niklas Thompson are acknowledged for assistance with X-ray analysis. Dr. Mona Shahgholi and Naseem Torian are thanked for mass spectrometry assistance. Dr. Scott Virgil is thanked for assistance with instrumentation. The authors declare no conflict of interest.

Attached Files

Accepted Version - nihms915640.pdf

Supplemental Material - anie201707015-sup-0001-SI1.pdf


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