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Issue 11, 2011
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Intramolecular catalytic asymmetric carbon–hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches

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Abstract

The synthetic potential of highly directional formal insertion of a carbene between carbon and hydrogen of a carbon–hydrogen bond has recently been developed for intramolecular reactions that lead to compounds of biological and medicinal interest. Stereoselective and regiocontrolled intramolecular processes from diazoacetate reactants, catalyzed by dirhodium(II) compounds with chiral carboxamidate ligands, provide efficient and selective access to compounds as diverse as enterolactone, baclofen, imperanene, xylolactone, and rolipram. A comparison of the C–H insertion methodology with alternative approaches is presented.

Graphical abstract: Intramolecular catalytic asymmetric carbon–hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches

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Article information


Submitted
08 Sep 2010
First published
07 Feb 2011

Org. Biomol. Chem., 2011,9, 4007-4016
Article type
Perspective

Intramolecular catalytic asymmetric carbon–hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches

M. P. Doyle, M. Ratnikov and Y. Liu, Org. Biomol. Chem., 2011, 9, 4007
DOI: 10.1039/C0OB00698J

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