Synthesis of β-monosubstituted α,β-unsaturated amides with Z-selectivity using diphenylphosphonoacetamides
✍ Scribed by Satoshi Kojima; Tsugihiko Hidaka; Yuko Ohba
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 129 KB
- Volume
- 15
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20054
No coin nor oath required. For personal study only.
✦ Synopsis
The utility of diphenylphosphonoacetamides [(PhO) 2 P(O)CH 2 CONRR ] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a:
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## Abstract For Abstract see ChemInform Abstract in Full Text.
Stereoselective b-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield a,b-unsaturated amides 2, in which the C C bond is di-tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the corresponding lithium enolates of a-chloroamide