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Published July 9, 2018 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation

Abstract

The development of the first enantioselective transition‐metal‐catalyzed allylic alkylation providing access to acyclic products bearing vicinal all‐carbon quaternary centers is disclosed. The iridium‐catalyzed allylic alkylation reaction proceeds with excellent yields and selectivities for a range of malononitrile‐derived nucleophiles and trisubstituted allylic electrophiles. The utility of these sterically congested products is explored through a series of diverse chemo‐ and diastereoselective product transformations to afford a number of highly valuable, densely functionalized building blocks, including those containing vicinal all‐carbon quaternary stereocenters.

Additional Information

© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: April 25, 2018; Accepted manuscript online: May 11, 2018; Version of record online: June 11, 2018. 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 and Dr. Lawrence Henling are acknowledge for assistance with X-ray analysis. Dr. Mona Shahgholi and Naseem Torian are thanked for mass spectrometry assistance. Dr. David VanderVelde is thanked for assistance with NMR analysis.

Attached Files

Accepted Version - nihms967832.pdf

Supplemental Material - anie201804820-sup-0001-si1.pdf

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Additional details

Created:
August 19, 2023
Modified:
October 18, 2023