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Stereoselective Synthesis of Z -α-Aryl-α,β-unsaturated Esters
✍ Scribed by Mani, Neelakandha S.; Mapes, Christopher M.; Wu, Jiejun; Deng, Xiaohu; Jones, Todd K.
- Book ID
- 126761212
- Publisher
- American Chemical Society
- Year
- 2006
- Tongue
- English
- Weight
- 68 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
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.
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