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

Angewandte Chemie
J Caleb HethcoxBrian M Stoltz

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.

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Citations

May 14, 2019·Angewandte Chemie·Xi-Jia LiuShu-Li You
Aug 7, 2018·Chemical Science·Rahul SarkarSantanu Mukherjee
Mar 2, 2021·Journal of the American Chemical Society·Mayuko IsomuraErick M Carreira
Apr 7, 2021·Organic Letters·Sankash Mitra, Santanu Mukherjee
Nov 4, 2020·Journal of the American Chemical Society·Ye WangShu-Li You
Jun 28, 2019·Accounts of Chemical Research·Simon L RösslerErick M Carreira
Aug 14, 2019·Journal of the American Chemical Society·Franz-Lucas HautThomas Magauer
Jul 15, 2020·Journal of the American Chemical Society·Min HanPeng Cao
Aug 27, 2019·The Journal of Organic Chemistry·Matteo FaltraccoEelco Ruijter
Sep 22, 2018·Journal of the American Chemical Society·Santanu Panda, Joseph M Ready
Oct 30, 2019·The Journal of Organic Chemistry·Qian WanYu Du
Jul 19, 2019·Journal of the American Chemical Society·Tobias SandmeierErick M Carreira
Dec 26, 2018·Chemical Reviews·Qiang ChengShu-Li You
Apr 18, 2020·Organic Letters·Samir GhoraiChangkun Li

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