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Synthesis of Isotopically Labeled (E)-β,γ-Unsaturated Esters with Total or High Diastereoselectivity by Using Samarium Diiodide

✍ Scribed by José M. Concellón; Pablo L. Bernad; Humberto Rodríguez-Solla

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 73 KB
Volume: 40
Category: Article
ISSN: 0044-8249
DOI: 10.1002/1521-3773(20011015)40:20<3897::aid-anie3897>3.0.co;2-o

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✦ Synopsis

A simple, efficient, highly diastereoselective method for preparing (E)-α,δ-dideuterio-β,γ-unsaturated esters: SmI -promoted reduction/elimination of α-halo-β-hydroxy-γ,δ-unsaturated esters in the presence of D O. This provides the desired products in which the C-C double bond is generated with total or high diastereoselectivity.

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