72284-21-0Relevant articles and documents
Scalable Preparation of Methylated Ando-Type Horner-Wadsworth-Emmons Reagent
Bressin, Robert K.,Driscoll, Julia L.,Wang, Yanping,Koide, Kazunori
, p. 274 - 277 (2019)
The Horner-Wadsworth-Emmons (HWE) reactions are vital to the chemical synthesis of complex molecules, forging a carbon-carbon double bond in the generation of α,β-unsaturated enoates from aldehydes or ketones. Despite their frequent use, the Z-stereoselective formation of α,β-unsaturated esters from aldehydes have been mostly limited to the use of the commercially available Still-Gennari reagent. Ando developed an alternative reagent to achieve the same formation with less expensive reagents. However, an α-methylated Ando-HWE reagent has remained difficult to prepare, hindering a reliable route to α,β-disubstituted Z-enoates. Here, we report the development of a preparative synthesis of a methylated Ando-HWE reagent for the highly Z-selective HWE reaction. Costing $0.49/mmol, this synthesis is significantly cheaper than the currently available Still-Gennari reagent ($11/mmol, Millipore Sigma 2018). The purification procedure does not require chromatography, with recrystallization as the only purification method, making it highly amenable to large-scale production.
Hantzsch Ester as a Photosensitizer for the Visible-Light-Induced Debromination of Vicinal Dibromo Compounds
Chen, Wenxin,Tao, Huachen,Huang, Wenhao,Wang, Guoqiang,Li, Shuhua,Cheng, Xu,Li, Guigen
supporting information, p. 9546 - 9550 (2016/07/14)
The debromination of vicinal dibromo compounds to generate alkenes usually requires harsh reaction conditions and the addition of catalysts. Just recently the visible-light-induced debromination of vicinal dibromo compounds emerged as a possible alternative to commonly used methods, but the substrate scope of this reaction is limited and a photocatalyst is necessary for the successful conversion of the starting compounds. A catalyst-free visible-light-induced debromination of vicinal dibromo compounds with a base-activated Hantzsch ester as photosensitizer is reported. The method has a wide substrate scope and a broad functional-group compatibility.
Z-selective Horner-Wadsworth-Emmons reaction of (α-substituted ethyl (Diarylphosphono)acetates with aldehydes
Ando, Kaori
, p. 8411 - 8416 (2007/10/03)
New Horner-Wadsworth-Emmons reagents, ethyl 2- (diarylphosphono)propionates (2), ethyl 2-(diarylphosphono)hexanoates (3), and ethyl 2-(diarylphosphono)-3-methylbutanoates (4) were prepared by alkylation of ethyl (diarylphosphono)acetates. The reaction of
