Stereoselective synthesis of α-phenylchalcogeno-α,β-unsaturated esters
✍ Scribed by Claudio C. Silveira; Antonio L. Braga; Robson B. Guerra
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 123 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Ethyl a-phenylchalcogeno a,b-unsaturated esters were prepared in a stereoselective manner by the reaction of ethyl propiolates with organocuprates, followed by the reaction with the appropriate electrophilic organosulfur, organoselenium or organotellurium source.
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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