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• W2952316053 abstract "An asymmetric synthesis of regio- and stereoselectively deuterium-labelled L-leucine was examined using 4-hydroxy-L-proline as a chiral template. An enol triflate of 4-oxoproline prepared from 4-hydroxyproline was effectively methylated by a Gilman reagent to afford a 4-methyl-3,4-dehydroproline derivative. Then, a catalytic deuteration of the dehydroproline followed by RuO4-oxidation gave a deuterated 4-methylpyroglutamic acid derivative that could easily be converted to (2S,3S,4R)-leucine-3,4,5,5,5-d5 via a base-promoted ring opening and a reductive deuteration of the terminal carboxyl moiety. This strategy was also applied to the stereoselective synthesis of (2S,3S,4S)-[3,4,5,5,5-D5]leucine." @default.
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• W2952316053 date "1998-03-01" @default.
• W2952316053 modified "2023-10-03" @default.
• W2952316053 title "Stereoselective deuterium-labelling of diastereotopic methyl and methylene protons of L-leucine" @default.
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• W2952316053 doi "https://doi.org/10.1016/s0040-4039(98)00037-9" @default.
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