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The selective functionalization of carbon-carbon sigma bonds is a synthetic strategy that offers uncommon retrosynthetic disconnections. Despite progress in CC activation and its great importance, the development of asymmetric reactions lags behind. Rhodium(I)-catalyzed selective oxidative additions into enantiotopic CC bonds in cyclobutanones are reported. Even operating at a reaction temperature of 130 degrees 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.
Kay Severin, Nicolai Cramer, Carl Thomas Bormann, Jin Fay Tan
Bastian Antoine Rodolphe Claude Muriel
Xile Hu, Chao Fan, Srikrishna Bera, Zhikun Zhang