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

Title Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.
Authors C. Hethcox; S. Shockley; B. Stoltz
Journal Angew Chem Int Ed Engl
DOI 10.1002/anie.201804820
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.

Citation C. Hethcox; S. Shockley; B. Stoltz.Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.. Angew Chem Int Ed Engl. 2018. doi:10.1002/anie.201804820

Related Elements

Iridium

See more Iridium products. Iridium (atomic symbol: Ir, atomic number: 77) is a Block D, Group 9, Period 6 element with an atomic weight of 192.217. The number of electrons in each of iridium's shells is [2, 8, 18, 32, 15, 2] and its electron configuration is [Xe] 4f14 5d7 6s2. Iridium Bohr ModelThe iridium atom has a radius of 136 pm and a Van der Waals radius of 202 pm. Iridium was discovered and first isolated by Smithson Tennant in 1803. In its elemental form, Iridium has a silvery white appearance. Iridium is a member of the platinum group of metals.Elemental Iridium It is the most corrosion resistant metal known and is the second-densest element (after osmium). It will not react with any acid and can only be attacked by certain molten salts, such as molten sodium chloride. Iridium is found as an uncombined element and in iridium-osmium alloys. Iridium's name is derived from the Greek goddess Iris, personification of the rainbow, on account of the striking and diverse colors of its salts.

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