1133378-77-4

Upstream product

• 817637-39-1 (E)-methyl 3-(4-methoxybenzyloxy)acrylate 

Downstream Products

• 1080004-46-1 (E)-3-(4-methoxybenzyloxy)allyl 2-(1,3-dioxoisoindolin-2-yl)acetate 
• 1255467-14-1 (E)-3-(4-methoxybenzyloxy)allyl 2-(bis(tert-butoxycarbonyl)amino)acetate 
• 1354623-45-2 4-benzyl 3-tert-butyl (2S,4S)-2-tert-butyl-4-((R)-1-(4-methoxybenzyloxy)allyl)oxazolidine-3,4-dicarboxylate 
• 1354623-46-3 4-benzyl 3-tert-butyl (2R,4R)-2-tert-butyl-4-((S)-1-(4-methoxybenzyloxy)allyl)oxazolidine-3,4-dicarboxylate 
• 1354623-40-7 3-tert-butyl 4-methyl (2R,4R)-2-tert-butyl-4-((S)-1-(4-methoxybenzyloxy)allyl)oxazolidine-3,4-dicarboxylate 
• 1354623-23-6 3-tert-butyl 4-((E)-3-(4-methoxybenzyloxy)allyl) (2R,4S)-2-tert-butyloxazolidine-3,4-dicarboxylate 
• 1354623-29-2 3-tert-butyl 4-((E)-3-(4-methoxybenzyloxy)allyl) (2S,4R)-2-tert-butyloxazolidine-3,4-dicarboxylate 

Relevant academic research and scientific papers

Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers

This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantioselective and site-selective coupling with acyclic aryl enol ethers

Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G

The Ireland - Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.

An Ireland-Claisen approach to β-alkoxy α-amino acids

(Chemical Equation Presented) A diastereoselective Ireland-Claisen approach to β-alkoxy α-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.