Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp (2) )-H Alkylation with Nitroalkanes

We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp(2))-H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing a sterically hindered urea at the C-9 position, was fou...

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Bibliographic Details
Published inSynlett Vol. 29; no. 16; pp. 2155 - 2160
Main Authors Dinh, Andrew N., Noorbehesht, Ryan R., Toenjes, Sean T., Jackson, Amy C., Saputra, Mirza A., Maddox, Sean M., Gustafson, Jeffrey L.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BIARYL ATROPISOMERS
chirality
ENANTIOSELECTIVE SYNTHESIS
DRUG DISCOVERY
ARYLATION
ELECTRONIC CIRCULAR-DICHROISM
asymmetric catalysis
phase-transfer catalysis
atropisomerism
DYNAMIC KINETIC RESOLUTION
TARGET SELECTIVITY
BROMINATION
INCREASE
alkylation
SYSTEMS
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Summary:We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp(2))-H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing a sterically hindered urea at the C-9 position, was found to effect atroposelective C(sp(2))-H alkylation with moderate to good enantioselectivities across several naphthoquinone-containing diaryl ethers. Products could then be isolated in >95:5 er after one round of trituration. For several substrates that were evaluated, we obtained nitroethylated products in similar yields and selectivities.
Bibliography:NIH RePORTER
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1609581