Bayeh, Liela; Le, Phong Q.; Tambar, Uttam K. published an article in Nature (London, United Kingdom). The title of the article was 《Catalytic allylic oxidation of internal alkenes to a multifunctional chiral building block》.Recommanded Product: (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene The author mentioned the following in the article:
The stereoselective oxidation of hydrocarbons is one of the most notable advances in synthetic chem. over the past fifty years. Inspired by nature, enantioselective dihydroxylations, epoxidations and other oxidations of unsaturated hydrocarbons have been developed. More recently, the catalytic enantioselective allylic carbon-hydrogen oxidation of alkenes has streamlined the production of pharmaceuticals, natural products, fine chems. and other functional materials. Allylic functionalization provides a direct path to chiral building blocks with a newly formed stereocenter from petrochem. feedstocks while preserving the olefin functionality as a handle for further chem. elaboration. Various metal-based catalysts have been discovered for the enantioselective allylic carbon-hydrogen oxidation of simple alkenes with cyclic or terminal double bonds. However, a general and selective allylic oxidation using the more common internal alkenes remains elusive. Here we report the enantioselective, regioselective and E/Z-selective allylic oxidation of unactivated internal alkenes via a catalytic hetero-ene reaction with a chalcogen-based oxidant [e.g., I + sulfurimide PhSO2N:S:O → II (68% yield, 96:4 er, > 20:1 rr) in presence of SbCl5 and a chiral BINOL derivative]. Our method enables non-sym. internal alkenes to be selectively converted into allylic functionalized products with high stereoselectivity and regioselectivity. Stereospecific transformations of the resulting multifunctional chiral building blocks highlight the potential for rapidly converting internal alkenes into a broad range of enantioenriched structures that can be used in the synthesis of complex target mols. The experimental process involved the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Recommanded Product: (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)
(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.Recommanded Product: (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneHalogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com