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The low yield obtained from reaction of 2b, compared with that obtained from 2 a, could be a consequence of the lower stability of substrate 2b and adduct 8b in relation to the corresponding a isomers, under the reaction conditions
-
The low yield obtained from reaction of 2b, compared with that obtained from 2 a, could be a consequence of the lower stability of substrate 2b and adduct 8b in relation to the corresponding a isomers, under the reaction conditions.
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57
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77951951981
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note
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2Ph) was similar to that of the starting allene/sulfinate ratio.
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59
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77951946372
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3 and water) to those used for Lu's reactions (under these conditions only traces of cyclopentenes are obtained), which determine a different reaction course
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3 and water) to those used for Lu's reactions (under these conditions only traces of cyclopentenes are obtained), which determine a different reaction course.
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60
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60949108432
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For other reactions of a-methyl allenoates with electron-deficient olefins catalysed by tetra-n-butylammonium fluoride (to afford 2-alkynyl-2-substituted glutaric acid derivatives), see: L.-P. Liu, B. Xu, G. B. Hammond, Org. Lett. 2008, 10, 3887-3890.
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77951969975
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The ee values were determined by HPLC employing a Daicel Chiralpack AD column, with hexane and isopropyl alcohol as the eluents
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The ee values were determined by HPLC employing a Daicel Chiralpack AD column, with hexane and isopropyl alcohol as the eluents.
-
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62
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77951961720
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Although no adducts of 2 b with alienes 4 and 5 were obtained, the enantiomers of 13a and 14a could be accessible by this route
-
Although no adducts of 2 b with alienes 4 and 5 were obtained, the enantiomers of 13a and 14a could be accessible by this route.
-
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63
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77951955452
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note
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Preliminary studies of these reactions have been performed. Reaction of racemic (±)-6 with diethyl malonate only provides one diastereoisomer, which results from the approach of the nucleophile to the convex face of the bicyclic system. The application of these products to the synthesis of a range of known and novel structures is under investigation.
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CCDC-755291 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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CCDC-755291 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
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