Towards a Catalytic Atroposelective Synthesis of Diaryl Ethers via C( sp 2 )-H Alkylation Using Nitroalkanes

Herein we report studies towards a small molecule catalytic approach to access atropisomeric diaryl ethers that proceeds via a C( )-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...

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Bibliographic Details
Published in:Synlett 2018-10, Vol.29 (16), p.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: Article
Language:English
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Summary:Herein we report studies towards a small molecule catalytic approach to access atropisomeric diaryl ethers that proceeds via a C( )-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( )-H alkylation with moderate to good enantioselectivities across several naphthoquinone-containing diaryl ethers. Products can then be isolated in greater than 95:5 er after one round of trituration. For several substrates that were evaluated we observed a 'nitroethylated' product in similar yields and selectivities.
ISSN:0936-5214
DOI:10.1055/s-0037-1609581