Selective carbon-carbon bond cleavage for the stereoselective synthesis of acyclic systems

Ilan Marek*, Ahmad Masarwa, Pierre Olivier Delaye, Markus Leibeling

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

280 Scopus citations

Abstract

(Figure Presented) 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.

Original languageAmerican English
Pages (from-to)414-429
Number of pages16
JournalAngewandte Chemie - International Edition
Volume54
Issue number2
DOIs
StatePublished - 7 Jan 2015
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • C-C activation
  • Carbometalation
  • Ring opening
  • Stereocenters
  • Strained molecules

Fingerprint

Dive into the research topics of 'Selective carbon-carbon bond cleavage for the stereoselective synthesis of acyclic systems'. Together they form a unique fingerprint.

Cite this