Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Chiral diethylzinc complexes with diamine ligands: synthesis, crystal structure and enantioselective solvent-free alkylation
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2005 (English)In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 690, no 16, 3846-3853 p.Article in journal (Refereed) Published
Abstract [en]

In search for conglomerates of stereochemically labile organometallic reagents, three new complexes between diethylzinc and diamine ligands have been synthesized and structurally characterized by single-crystal X-ray diffraction methods. Ligands include N,N,N',N'-tetraethylethylenediamine (teeda), N-isopropyl-N,N',N'-trimethylethylenediamine (itmeda), and (-)-sparteine (spa). Diethylzinc forms monomeric complexes, exhibiting a distorted tetrahedral coordination geometry around zinc in all three complexes, viz. [ZnEt(2)(teeda)] (1), [ZnEt(2)(itmeda)] (2), and [ZnEt(2)(spa)] (3). Both 1 and 2 are stereochemically labile and exhibit chiral complexes, displaying different types of conformational chirality, but they form racemic crystals. By using the chiral crystals of 3 in a nucleophilic addition to benzaldehyde in the absence of solvent at low temperature, an increase in ee from approximately 8 to 10% was obtained (compared to the same reaction in solution). It thus seems feasible, not only to retain the enantioselectivity obtained in solution, but perhaps even to increase the ee by using solventless reactions.

Place, publisher, year, edition, pages
2005. Vol. 690, no 16, 3846-3853 p.
Keyword [en]
conglomerate, diethylzinc, N-chirogenic, solid-state reaction, solvent-free reaction
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-38298DOI: 10.1016/j.jorganchem.2005.05.015ISI: 000231945800027Scopus ID: 2-s2.0-23844543394OAI: oai:DiVA.org:kth-38298DiVA: diva2:436648
Note
QC 20110824Available from: 2011-08-24 Created: 2011-08-24 Last updated: 2017-12-08Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Wingstrand, Erica
By organisation
Organic Chemistry
In the same journal
Journal of Organometallic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 48 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf