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Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry
- Source :
- Organic letters. 20(9)
- Publication Year :
- 2018
-
Abstract
- Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Aryl
Organic Chemistry
chemistry.chemical_element
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
chemistry
Organic chemistry
Lithium
Physical and Theoretical Chemistry
Racemization
Selenium
Alkyl
Carbanion
Subjects
Details
- ISSN :
- 15237052
- Volume :
- 20
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....95968b8133878c5f820c11c4ffbbf5f6