Highly Enantioselective Rhodium(I)-Catalyzed Activation of Enantiotopic Cyclobutanone C-C Bonds

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.


Published in:
Angewandte Chemie-International Edition, 53, 11, 3001-3005
Year:
2014
Publisher:
Weinheim, Wiley-V C H Verlag Gmbh
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2014-04-14, last modified 2018-03-17


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