title: Selective carbon-carbon bond cleavage for the stereoselective synthesis of acyclic systems.
abstract: 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 C-C 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.
authors.affiliation: Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel). chilanm@tx.technion.ac.il.
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
authors.forename: Ahmad
authors.initials: A
authors.lastname: Masarwa
authors.forename: Pierre-Olivier
authors.initials: PO
authors.lastname: Delaye
authors.forename: Markus
authors.initials: M
authors.lastname: Leibeling
keywords: CC activation; carbometalation; ring opening; stereocenters; strained molecules