202478-86-2Relevant articles and documents
Reaction of tert-Butyl Dibromoacetate or N,N-Diethyldibromoacetamide with Trialkylmanganate Providing an Alkylated Manganese Enolate
Inoue, Rie,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 910 - 911 (1998)
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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
Concellón, José M.,Bardales, Eva,Gómez, Cecilia
, p. 5323 - 5326 (2007/10/03)
Ring-opening of 3-aryl-2,3-epoxyamides 1 was achieved by using samarium diiodide and D2O, 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 α-chloroamides with aldehydes or ketones. When the reaction was carried out in the presence of H2O instead of D2O, the corresponding 3-aryl-2-hydroxyamides were isolated. The treatment of enantiopure 3-aryl-2,3-epoxyamides afforded optically active 3-aryl-2-hydroxyamides.