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Highly enantioselective rhodium(I)-catalyzed activation of enantiotopic cyclobutanone C-C bonds

Highly enantioselective rhodium(I)-catalyzed activation of enantiotopic cyclobutanone C-C bonds

Angewandte Chemie 53(11): 3001-3005

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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Accession: 053557870

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PMID: 24519918

DOI: 10.1002/anie.201311009

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