Synthesis of spirocyclic orthoesters by ‘anomalous’ rhodium(ii)-catalysed intramolecular C–H insertions

Organic & Biomolecular Chemistry(2018)

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摘要
A tetrahydropyranyl acetal bearing a proximal phenyl diazoketone substituent underwent Rh(II)-catalysed C-H insertion via an 'anomalous' C-O bond-forming, rather than C-C bond-forming, transformation, giving spirocyclic orthoesters. Density functional theory calculations with M06 show that the formation of these anomalous products involves hydride transfer to the rhodium carbene, giving an intermediate zwitterion which undergoes C-O bond formation in preference to C-C bond formation.
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spirocyclic orthoesters,synthesis
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