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- W4210679627 abstract "Enantioenriched seven-membered carbocycles are motifs in many molecules of structural and biological interest. We report a simple, practical, transition metal-free and mechanistically unusual method for the enantioselective synthesis of substituted cycloheptatrienes. By forming a coloured enolate with an appropriate absorption band and selectively irradiating in situ, we to initiate a tandem, asymmetric anionic and photochemical ring expansion of readily accessible N-benzylbenzamides. The cascade of reactions leading to the products entails enantioselective benzylic deprotonation with a chiral lithium amide, dearomatizing cyclization of the resulting configurationally defined organolithium to give an extended amide enolate, and photochemically induced formal [1,7]-sigmatropic rearrangement and 6π-electrocyclic ring-opening - the latter all evidently being stereospecific - to deliver enantioenriched cycloheptatrienes with embedded benzylic stereocentres." @default.
- W4210679627 created "2022-02-08" @default.
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- W4210679627 date "2022-01-01" @default.
- W4210679627 modified "2023-09-26" @default.
- W4210679627 title "Enantioselective one-carbon expansion of aromatic rings by simultaneous formation and chromoselective irradiation of a transient coloured enolate" @default.
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- W4210679627 doi "https://doi.org/10.1039/d1sc06684f" @default.
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