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Stereoselective deuterium-labelling of diastereotopic methyl and methylene protons of L-leucine

✍ Scribed by Makoto Oba; Tsutomu Terauchi; Akiko Miyakawa; Hisano Kamo; Kozaburo Nishiyama

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 229 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00037-9

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✦ Synopsis

An asymmetric synthesis of mgio-and stem3sdectively deutmum-labelled L-lcucine was eaamined using 4-hydmxy-L-proline as a chiral template. An enoi trifl~te of 4-oxol~line ~q3med from 4-hy&oxypmline was effectively methylat~ by a Gilman reagent to afford a 4-mcthyl-3,4dehydmpmline di~rivative. Then, a catalytic ~ion of the dehyckopmline followed by RuO,oxidation gave a deuterated 4-methylpymglutamic acid derivative that could easily be converted to (2S,3S,4R)-le~ne-3,4,5,5,5-dj via a bese4msnoted ring opening and a ~ve deute~ion of the tcxminal cad~oxyl moiety. This strategy was also applied to the stercoselective synthesis of (2S,3S,4S)- ieucine.

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