Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process.

Title Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process.
Authors K. Mori; R. Isogai; Y. Kamei; M. Yamanaka; T. Akiyama
Journal J Am Chem Soc
DOI 10.1021/jacs.8b02761
Abstract

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp)-H bond functionalization by an achiral catalyst (Yb(OTf), second [1,5]-hydride shift).

Citation K. Mori; R. Isogai; Y. Kamei; M. Yamanaka; T. Akiyama.Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process.. J Am Chem Soc. 2018. doi:10.1021/jacs.8b02761

Related Elements

Magnesium

Magnesium Bohr ModelSee more Magnesium products. Magnesium (atomic symbol: Mg, atomic number: 12) is a Block S, Group 2, Period 3 element with an atomic mass of 24.3050. The number of electrons in each of Magnesium's shells is [2, 8, 2] and its electron configuration is [Ne] 3s2. The magnesium atom has a radius of 160 pm and a Van der Waals radius of 173 pm. Magnesium was discovered by Joseph Black in 1775 and first isolated by Sir Humphrey Davy in 1808. Magnesium is the eighth most abundant element in the earth's crust and the fourth most common element in the earth as a whole. Elemental MagnesiumIn its elemental form, magnesium has a shiny grey metallic appearance and is an extremely reactive. It is can be found in minerals such as brucite, carnallite, dolomite, magnesite, olivine and talc. Commercially, magnesium is primarily used in the creation of strong and lightweight aluminum-magnesium alloys, which have numerous advantages in industrial applications. The name "Magnesium" originates from a Greek district in Thessaly called Magnesia.

Phosphorus

Phosphorus Bohr ModelSee more Phosphorus products. Phosphorus (atomic symbol: P, atomic number: 15) is a Block P, Group 15, Period 3 element. The number of electrons in each of Phosphorus's shells is 2, 8, 5 and its electronic configuration is [Ne] 3s2 3p3. The phosphorus atom has a radius of 110.5.pm and its Van der Waals radius is 180.pm. Phosphorus is a highly-reactive non-metallic element (sometimes considered a metalloid) with two primary allotropes, white phosphorus and red phosphorus its black flaky appearance is similar to graphitic carbon. Compound forms of phosphorus include phosphates and phosphides. Phosphorous was first recognized as an element by Hennig Brand in 1669 its name (phosphorus mirabilis, or "bearer of light") was inspired from the brilliant glow emitted by its distillation.

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