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The F-C reaction of indole 3a with methyl 3,3,3-trifluoropyruvate 4b afforded the product 5b in good yield in dichloromethane and in tetrahydrofuran. However, the enantioselectivities were lower (28 and 45% ee, respectively) in these instances.
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15
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15044359675
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note
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The absolute stereochemistry of (2S)-2-(4-chloroindole-3-yl)-3,3,3- trifluoro-2-hydroxy propionic acid ethyl ester has been assigned unambiguously by X-ray crystallography, and the absolute stereochemistry of compound 5a was assigned by analogy; see ref 6b.
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15044356937
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note
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This result is in contrast to the bisoxazoline copper(II) complex-catalyzed reactions in which substitution of the indole nitrogen does not lower the enantioselectivity of the reaction; see ref 6b.
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See the supporting information for ref 10.
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