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Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide. Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity

✍ Scribed by José M. Concellón; Eva Bardales; Cecilia Gómez

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 110 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01201-2

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✦ Synopsis

Ring-opening of 3-aryl-2,3-epoxyamides 1 was achieved by using samarium diiodide and D 2 O, yielding 3-aryl-3-deuterio-2-hydroxyamides 2 with total regioselectivity. The starting compounds 1 were easily prepared by reaction of the corresponding lithium or potassium enolates of a-chloroamides with aldehydes or ketones. When the reaction was carried out in the presence of H 2 O instead of D 2 O, the corresponding 3-aryl-2-hydroxyamides were isolated. The treatment of enantiopure 3-aryl-2,3epoxyamides afforded optically active 3-aryl-2-hydroxyamides.

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