Journal article
Highly enantioselective rhodium(I)-catalyzed activation of enantiotopic cyclobutanone C-C bonds.
- Souillart L Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.
- Parker E
- Cramer N
- 2014-02-13
Published in:
- Angewandte Chemie (International ed. in English). - 2014
English
The selective functionalization of carbon-carbon σ bonds is a synthetic strategy that offers uncommon retrosynthetic disconnections. Despite progress in C-C activation and its great importance, the development of asymmetric reactions lags behind. Rhodium(I)-catalyzed selective oxidative additions into enantiotopic C-C bonds in cyclobutanones are reported. Even operating at a reaction temperature of 130 °C, the process is characterized by outstanding enantioselectivity with the e.r. generally greater than 99.5:0.5. The intermediate rhodacycle is shown to react with a wide variety of tethered olefins to deliver complex bicyclic ketones in high yields.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.201311009
- PMID 24519918
- Persistent URL
- https://sonar.rero.ch/global/documents/99460
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