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Oxidative Cyclization of Naphtholic Sulfonamides Mediated by a Chiral Hypervalent Iodine Reagent: Asymmetric Synthesis versus Resolution
- Source :
- Synlett. 30:1222-1227
- Publication Year :
- 2019
- Publisher :
- Georg Thieme Verlag KG, 2019.
-
Abstract
- A chiral aryl iodide promotes the enantioselective oxidative cyclization of 1-naphtholic sulfonamides, albeit in moderate ee and low yield. The products tend to crystallize as conglomerates. Recrystallization thus increases their ee to > 99% ee. This highly enantioenriched material provides seed crystals for the resolution of the racemate (prepared in high yield by oxidative cyclization with (diacetoxyiodo)benzene in trifluoroacetic acid) by coupled preferential crystallization. This enables the production of significant quantities of highly enantioenriched products, despite the low efficiency of the enantioselective reaction.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Aryl
Organic Chemistry
Iodide
Enantioselective synthesis
Hypervalent molecule
chemistry.chemical_element
010402 general chemistry
Iodine
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
chemistry
Reagent
Trifluoroacetic acid
Organic chemistry
Benzene
Subjects
Details
- ISSN :
- 14372096 and 09365214
- Volume :
- 30
- Database :
- OpenAIRE
- Journal :
- Synlett
- Accession number :
- edsair.doi...........b80615392893ce3330a46b280db87aec