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,
Synthesis of α,β-γ,δ-unsaturated sulfones and sulfoxides via the Horner-Emmons reaction
✍ Scribed by B. E. de Jong; H. de Koning; H. O. Huisman
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 508 KB
- Volume
- 100
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
α,β‐γ,δ‐Unsaturated sulfones and sulfoxides have been prepared via the Horner‐Emmons reaction of α,β‐unsaturated carbonyl compounds with α‐phosphoryl sulfones and sulfoxides.
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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