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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
42
Identifiers
DOI: 10.1016/s0040-4039(02)01762-8

Abstract

Abstract 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-γ-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the β-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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