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46949104671
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Report on non-chiral hydrogen bond donor catalysts based on 4,5-diamino-9,9-dimethylxanthene skeleton, see: F.M. Muniz, V.A. Montero, Á.L. Fuentes de Arriba, L. Simón, C. Raposo, and J.R. Morán Tetrahedron Lett. 49 2008 5050
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11
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0035799157
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For reviews on the multimetallic bifunctional asymmetric catalysis, see: G.J. Rowlands Tetrahedron 57 2001 1865
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Rowlands, G.J.1
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15
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37649020600
-
-
Compound 2 was obtained in 75% yield, accompanied by formation of the di-Boc derivative (11%) and the recovery of 1 (10%). The di-Boc derivative was easily transformed into 1 in quantitative yield under basic conditions. For a reference of selective protection of 4,5-diamino-9,9-dimethylxanthenes, see: F.M. Muniz, L. Simón, S. Sáez, C. Raposo, and J.R. Morán Tetrahedron Lett. 49 2007 790
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16
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79251601165
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Partial racemization occurred when N,N-dimethyl (S)-phenylalanine was directly utilized for the coupling reaction
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Partial racemization occurred when N,N-dimethyl (S)-phenylalanine was directly utilized for the coupling reaction.
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17
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0142072631
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Precedent examples of asymmetric conjugate addition of 1,3-diketones to nitroalkenes to construct an all-carbon quaternary carbon center: T. Okino, Y. Hoashi, T. Furukawa, X. Xu, and Y. Takemoto J. Am. Chem. Soc. 127 2005 119
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79251599099
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See also Refs. 8d,e,g,j
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See also Refs. 8d,e,g,j
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40
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53549110221
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47
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79251599150
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No reaction occurred when 2-acetylcyclohexanone was used as the nucleophile
-
No reaction occurred when 2-acetylcyclohexanone was used as the nucleophile.
-
-
-
-
48
-
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79251593517
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Asymmetric conjugate addition of acetylacetone to 6a using (S)-proline-derived catalyst 5m gave (R)-7a in 65% yield with 71% ee (4 °C, 96 h), analogous to the case of (S)-phenylalanine-derived catalyst 5d (Table 1, entry 4)
-
Asymmetric conjugate addition of acetylacetone to 6a using (S)-proline-derived catalyst 5m gave (R)-7a in 65% yield with 71% ee (4 °C, 96 h), analogous to the case of (S)-phenylalanine-derived catalyst 5d (Table 1, entry 4).
-
-
-
-
49
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84962467066
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Another possibility that 1,3-dicarbonyl compounds interact with the urea catalyst based on a 4,5-diaminoxanthene scaffold through multiple hydrogen bonds would not be excluded at the present stage. For the theoretical studies of the mode of interaction between bifunctional thiourea derivatives and 1,3-dicarbonyl compounds in asymmetric conjugate addition to nitroalkenes, see: A. Hamza, G. Schubert, T. Soóe, and I. Pápai J. Am. Chem. Soc. 128 2006 13151 See also reference 11f
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50
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79251596510
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At the present stage, the origin of enantiofacial discrimination of the prochiral enolate is unknown
-
At the present stage, the origin of enantiofacial discrimination of the prochiral enolate is unknown.
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