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Enantioselective Metalation of N,N-Diisopropylferrocenecarboxamide and Methyl Ferrocenecarboxylate Using Lithium-Metal Chiral Bases
- Dayaker, G. (författare)
- Tilly, D. (författare)
- Chevallier, F. (författare)
- visa fler...
- Gros, P. C. (författare)
- Mongin, F. (författare)
- visa färre...
- (creator_code:org_t)
- 2012-09-07
- 2012
- Engelska.
- Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X. ; :30, s. 6051-6057
- Tidskriftsartikel (refereegranskat)
Abstract
Ämnesord
Stäng
- 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
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Nyckelord
- 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
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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- European Journal of Organic Chemistry (Sök värdpublikationen i LIBRIS)
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- Av författaren/redakt...
- Dayaker, G.
- Tilly, D.
- Chevallier, F.
- Hilmersson, Göra ...
- Gros, P. C.
- Mongin, F.
- Om ämnet
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- NATURVETENSKAP
- NATURVETENSKAP
- och Kemi
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- European Journal ...
- Av lärosätet
- Göteborgs universitet
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