441019-86-9Relevant academic research and scientific papers
Asymmetric synthesis of 4′-ethoxy-2′,3′-didehydro-2′, 3′-dideoxynucleosides by palladium-catalyzed kinetic discrimination between the corresponding diastereoisomeric lactol acetates
Hegedus, Louis S.,Hervert, Katherine L.,Matsui, Satoshi
, p. 4076 - 4080 (2002)
4′-Substituted nucleoside analogues have been synthesized using palladium-catalyzed asymmetric allylic amination conditions. A kinetic discrimination between the diastereomeric lactol acetates (3) produced the desired aminated products (6a-d) and recovered acetate (α-3) in high yields and 97:3 diastereoselectivity. Epimerization of the recovered lactol acetate (α-3) produced a 60:40 α/β mixture of (3), which could be resubjected, in principle, to the palladium-catalyzed asymmetric allylic amination conditions.
