Highly Enantioselective Rhodium(I)‐Catalyzed Activation of Enantiotopic Cyclobutanone CC Bonds |
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Authors: | Laetitia Souillart Dr Evelyne Parker Prof?Dr Nicolai Cramer |
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Institution: | Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa |
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Abstract: | 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. |
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Keywords: | asymmetric catalysis C C activation cyclobutanone rearrangement rhodium |
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