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

Author(s) Hethcox, C.; Shockley, S.; Stoltz, B.
Journal Angew Chem Int Ed Engl
Date Published 2018 May 11

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.

DOI 10.1002/anie.201804820
ISSN 1521-3773
Citation Angew Chem Int Ed Engl. 2018.

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