AI Article Synopsis
- The study demonstrates a gold(I)-catalyzed method using a chiral phosphine ligand for the efficient and highly enantioselective dearomatization of phenols.
- The reaction is versatile, allowing substitutions on all benzene positions and accommodating various substituents, including strong electron-withdrawing groups and bulky carbon groups.
- High yields (up to 99%) and exceptional enantiomeric excess (up to 99%) are achieved for different substrate types like spirocyclohexadienone derivatives.
Article Abstract
By employing a chiral bifunctional phosphine ligand, a gold(I)-catalyzed efficient and highly enantioselective dearomatization of phenols is achieved via versatile metal-ligand cooperation. The reaction is proven to be remarkably general in scope, permitting substitutions at all four remaining benzene positions, accommodating electron-withdrawing groups including strongly deactivating nitro, and allowing carbon-based groups of varying steric bulk including tert-butyl at the alkyne terminus. Moreover, besides N-(o-hydroxyphenyl)alkynamides, the corresponding ynoates and ynones are all suitable substrates. Spirocyclohexadienone-pyrrol-2-ones, spirocyclohexadienone-butenolides, and spirocyclohexadenone-cyclopentenones are formed in yields up to 99 % and with ee up to 99 %.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10528085 | PMC |
| http://dx.doi.org/10.1002/anie.202309256 | DOI Listing |
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