New polymer-supported phosphonate reagents for the synthesis of Z-α,β-unsaturated esters
✍ Scribed by Kaori Ando; Yusaku Suzuki
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 358 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
New polymer-supported phosphonate reagents have been prepared and evaluated for the synthesis of Za,b-unsaturated esters.
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It has been shown that over-all conversions of carbonyl compounds to olefins, similar to the well known "Wittig" reaction, could be effected using silicon-substituted carbanions 1 . Recently, an alkyl lithiomethylacetate was reported to be an excellent reagent for the synthesis of a,%-unsaturated ca
A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH 4 in EtOH was developed. The one-pot reaction gave a-fluoro-a,b-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction
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