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33748063010
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For an example of asymmetric catalysis with an α-formyl amide, see:, During the completion of this manuscript, the asymmetric intramolecular arylation of α-keto amides was reported
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For an example of asymmetric catalysis with an α-formyl amide, see:, D. A. Evans, Y. Aye, J. Am. Chem. Soc. 2006, 128, 11034. During the completion of this manuscript, the asymmetric intramolecular arylation of α-keto amides was reported
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79961224085
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Racemic nitroaldol products of keto amides have been obtained by using catalytic amounts of diethyl- or triethylamine
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44
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83755162339
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Nitroaldol products are known to easily decompose and racemize under basic and acidic conditions or upon heating
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Nitroaldol products are known to easily decompose and racemize under basic and acidic conditions or upon heating.
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45
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83755181330
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For desymmetrization of 1,3-propanediols and 1,2,3-propanetriols
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For desymmetrization of 1,3-propanediols and 1,2,3-propanetriols, see
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47
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79951545822
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83755171327
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This ligand is commercially available at Strem (cat. no. 07-0488), US Patent, 11/737,371, 2007
-
This ligand is commercially available at Strem (cat. no. 07-0488), US Patent, 11/737,371, 2007.
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58
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83755162338
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note
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We found that in most cases double condensation to generate a bisoxazolidine structure does not occur with a wide range of amino alcohols and diketones. In contrast, only one carbonyl group reacts even under harsh conditions to give a monooxazolidine, or other by-products are formed.
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83755181328
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note
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The absolute configuration of the nitroaldol products was confirmed by NMR analysis with a chiral solvating agent (see the Supporting Information).
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64
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83755171325
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note
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The nitroaldol reaction with N-propyl and N-benzyl 2-oxo-2- phenylacetamide gave the product in 92-95-% yield and 26-30-% ee.
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66
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77249133649
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67
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83755181324
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note
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Formation of the tBoc derivative of 25 and HPLC analysis on a chiral stationary phase (Chiralpak AD) showed that the ee value was slightly reduced from 90-% to 86-% after the two reduction steps (see the Supporting Information).
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