Sökning: onr:"swepub:oai:gup.ub.gu.se/166544" >
Enantioselective Me...
Enantioselective Metalation of N,N-Diisopropylferrocenecarboxamide and Methyl Ferrocenecarboxylate Using Lithium-Metal Chiral Bases
- Artikel/kapitelEngelska2012
Förlag, utgivningsår, omfång ...
Nummerbeteckningar
-
LIBRIS-ID:oai:gup.ub.gu.se/166544
-
https://gup.ub.gu.se/publication/166544URI
-
https://doi.org/10.1002/ejoc.201200965DOI
Kompletterande språkuppgifter
Ingår i deldatabas
Klassifikation
-
Ämneskategori:ref swepub-contenttype
-
Ämneskategori:art swepub-publicationtype
Anmärkningar
-
Enantioselective deprotonative metalations of substituted ferrocenes using mixed lithium-metal bases are described. Using N,N-diisopropylferrocenecarboxamide as substrate, magnesium, iron, cobalt, zinc, and cadmium were tested as metals in bis[(S)-1-phenylethyl]amido-based combinations; after interception of the metalated species with iodine, very high enantiomeric excess (96?%) but low yield was obtained with cobalt, whereas zinc and cadmium only gave 27 and 30?%?ee, respectively, but in excellent yields. The small alkyl groups methyl and ethyl were identified as particularly suitable in the reaction using the putative dialkyl bis[(S)-1-phenylethyl]amido-based lithium and dilithium zincates. The dimethyl dilithium zincate was selected for a study of dependency on the temperature, reaction time, and amount of base. Increased enantioselectivities with temperature, reaction time, and amount of base were noted (ee = 86?% at 0 degrees C after 2 h, 2 equiv. of base). The best result using methyl ferrocenecarboxylate as substrate was observed without alkyl ligand.
Ämnesord och genrebeteckningar
-
NATURVETENSKAP Kemi hsv//swe
-
NATURAL SCIENCES Chemical Sciences hsv//eng
-
Metalation
-
Chirality
-
Zinc
-
Lithium
-
Metallocenes
-
Sandwich complexes
-
deprotonative metalation
-
structural elucidation
-
ortho-lithiation
-
amide bases
-
ferrocenes
-
planar
-
zinc
-
chemistry
-
magnesium
-
nmr
-
ice d
-
1995
-
tetrahedron letters
-
v36
-
p6135
Biuppslag (personer, institutioner, konferenser, titlar ...)
-
Tilly, D.
(författare)
-
Chevallier, F.
(författare)
-
Hilmersson, Göran,1966Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology(Swepub:gu)xhilgo
(författare)
-
Gros, P. C.
(författare)
-
Mongin, F.
(författare)
-
Göteborgs universitetInstitutionen för kemi och molekylärbiologi
(creator_code:org_t)
Sammanhörande titlar
-
Ingår i:European Journal of Organic Chemistry: Wiley:30, s. 6051-60571434-193X
Internetlänk
Hitta via bibliotek
Till lärosätets databas