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Issue 2, 2018
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Synthesis of spirocyclic orthoesters by ‘anomalous’ rhodium(ii)-catalysed intramolecular C–H insertions

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Abstract

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.

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

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Supplementary files

Article information


Submitted
25 Aug 2017
Accepted
05 Dec 2017
First published
05 Dec 2017

Org. Biomol. Chem., 2018,16, 256-261
Article type
Paper

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

F. J. Lombard, R. J. Lepage, B. D. Schwartz, R. C. Johnston, P. C. Healy, E. H. Krenske and M. J. Coster, Org. Biomol. Chem., 2018, 16, 256
DOI: 10.1039/C7OB02123B

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