Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.

Title Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.
Authors S.Wook Kim; W. Lee; M.J. Krische
Journal Org Lett
DOI 10.1021/acs.orglett.7b00343
Abstract

Glycidols prepared via Sharpless asymmetric epoxidation participate in asymmetric redox-neutral carbonyl allylation with good levels of catalyst-directed diastereoselectivity. Equally stereoselective allylations may be performed from the aldehyde oxidation level using 2-propanol as the terminal reductant. An epoxide ring-opening reaction using AlMe3-n-BuLi is used to prepare the propionate-based stereotetrad spanning C17-C23 of dictyostatin, illustrating how this method may be applied to polyketide construction.

Citation S.Wook Kim; W. Lee; M.J. Krische.Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.. Org Lett. 2017. doi:10.1021/acs.orglett.7b00343

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.

Related Forms & Applications