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Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner–Wadsworth–Emmons reaction

✍ Scribed by Ando, Kaori; Okumura, Miho; Nagaya, Shigeo


Book ID
119991703
Publisher
Elsevier Science
Year
2013
Tongue
French
Weight
638 KB
Volume
54
Category
Article
ISSN
0040-4039

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The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-diethylphosphonoacetates with s-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO 2 CF 3 ) 2 and N-ethylpiperidine in the presence of an external chiral ligand,

Convenient procedure of Horner–Wadsworth
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A mild and practical procedure of Horner-Wadsworth-Emmons olefination promoted by lithium hydroxide and a-cyano phosphonates has been set up for the synthesis of a,b-unsaturated nitriles. The reaction conditions are tolerated by functionalized ketones and the exclusive formation of E-g-hydroxy a,b-u