Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 2, Pages 414-429Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405067
Keywords
CC activation; carbometalation; ring opening; stereocenters; strained molecules
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Funding
- Israel Science Foundation [140/12]
- European Research Council under the Seventh Framework Program of the European Community (ERC) [338912]
- Alexander von Humboldt Foundation
- Sir Michael and Lady Sobell Academic Chair
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Most of the efforts of organic chemists have been directed to the development of creative strategies to build carbon-carbon and carbon-heteroatom bonds in a predictable and efficient manner. In this Review, we show an alternative approach where challenging molecular skeletons could be prepared through selective cleavage of carbon-carbon bonds. We demonstrate that it has the potential to be a general principle in organic synthesis for the regio-, diastereo-, and even enantioselective preparation of adducts despite the fact that CC single bonds are among the least reactive functional groups. The development of such strategies may have an impact on synthesis design and can ultimately lead to new selective and efficient processes for the utilization of simple hydrocarbons.
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