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Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone

✍ Scribed by Zhaohua Yan; Robert Weaving; Philippe Dauban; Robert H. Dodd

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 265 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01762-8

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✦ Synopsis

The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-g-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the b-position. A key step of the strategy was a titanate-mediated transesterification of a dimethyl ester into a dibenzyl analogue, allowing efficient deprotection to the free amino acid by hydrogenolysis.

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