Intramolecular cation-pi interaction in organic synthesis
- PMID: 17728854
- DOI: 10.1039/b706512b
Intramolecular cation-pi interaction in organic synthesis
Abstract
Controlling molecular conformation is a significantly important issue in a wide variety of organic reactions because the ground state structure is significantly responsible for the transition one. As observed in enzymes and proteins, the cation-pi interaction plays a key role in the formation of the tertiary structure and the biochemical processes. Therefore, the cation-pi interaction would be a promising conformation-controlling tool not only in large molecules, but also in small molecules due to its stronger interaction force. This article describes the utility of the intramolecular cation-pi interaction in various organic syntheses with evidence for the existence of the cation-pi interactions.
Similar articles
-
Asymmetric Cu(II) catalyses for cycloaddition reactions based on π-cation or n-cation interactions.Chem Soc Rev. 2011 Jan;40(1):163-72. doi: 10.1039/b924478f. Epub 2010 Sep 6. Chem Soc Rev. 2011. PMID: 20820460 Review.
-
Evidence for the cation-pi interaction between Cu2+ and tryptophan.J Am Chem Soc. 2008 Nov 19;130(46):15266-7. doi: 10.1021/ja807010f. Epub 2008 Oct 22. J Am Chem Soc. 2008. PMID: 18939840
-
Intramolecular cation-pi interactions as the driving force to restrict the conformation of certain nucleosides.J Org Chem. 2010 Mar 19;75(6):1974-81. doi: 10.1021/jo902677s. J Org Chem. 2010. PMID: 20192191
-
Relative strength of cation-pi vs salt-bridge interactions: the Gtalpha(340-350) peptide/rhodopsin system.J Am Chem Soc. 2006 Jun 14;128(23):7531-41. doi: 10.1021/ja058513z. J Am Chem Soc. 2006. PMID: 16756308
-
Carbohydrates as synthetic tools in organic chemistry.Chemistry. 2007;13(31):8648-59. doi: 10.1002/chem.200701010. Chemistry. 2007. PMID: 17712826 Review.
Cited by
-
A UB3LYP and UMP2 theoretical investigation on unusual cation-pi interaction between the triplet state HB=BH (3 Sigma g-) and H+, Li +, Na +, Be 2+ or Mg 2+.J Mol Model. 2010 Apr;16(4):615-27. doi: 10.1007/s00894-009-0575-1. Epub 2009 Sep 2. J Mol Model. 2010. PMID: 19727862
-
Highly stereoselective ring expansion reactions mediated by attractive cation-n interactions.Angew Chem Int Ed Engl. 2008;47(33):6233-5. doi: 10.1002/anie.200801591. Angew Chem Int Ed Engl. 2008. PMID: 18613179 Free PMC article.
-
Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.J Org Chem. 2010 Feb 19;75(4):1235-43. doi: 10.1021/jo902574m. J Org Chem. 2010. PMID: 20095596 Free PMC article.
-
The Cation-π Interaction in Small-Molecule Catalysis.Angew Chem Int Ed Engl. 2016 Oct 4;55(41):12596-624. doi: 10.1002/anie.201600547. Epub 2016 Jun 22. Angew Chem Int Ed Engl. 2016. PMID: 27329991 Free PMC article. Review.
-
Ammonium catalyzed cyclitive additions: evidence for a cation-π interaction with alkynes.Chem Commun (Camb). 2016 Feb 7;52(11):2311-3. doi: 10.1039/c5cc08641h. Chem Commun (Camb). 2016. PMID: 26728333 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Research Materials
Miscellaneous