Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

Journal of the American Chemical Society
David A PetroneErick M Carreira

Abstract

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution products (93-99% ee) with complete regiocontrol (>50:1 rr in all cases) over the corresponding 1,3-diene isomers which are obtained predominantly when other metal catalysts are emplyed. The synthetic utility of the products obtained was highlighted in a variety of stereoselective transition metal-catalyzed difunctionalization reactions. Furthermore, a combination of experimental and theoretical studies provide support for a putative reaction mechanism wherein enantiodetermining C-C coupling occurs via nucleophilic attack on a highly planarized aryl butadienylium π-system that is coordinated to the Ir center in an η2-fashion.

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Citations

Mar 2, 2021·Journal of the American Chemical Society·Mayuko IsomuraErick M Carreira
Feb 21, 2019·Journal of the American Chemical Society·Mayuko IsomuraErick M Carreira
May 27, 2020·The Journal of Organic Chemistry·Runmin ZhaoYufen Zhao
Jun 28, 2019·Accounts of Chemical Research·Simon L RösslerErick M Carreira
Nov 20, 2018·Journal of the American Chemical Society·Patrick J MoonRylan J Lundgren
Sep 22, 2018·Journal of the American Chemical Society·Santanu Panda, Joseph M Ready
Dec 26, 2018·Chemical Reviews·Qiang ChengShu-Li You

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