190913-47-4Relevant academic research and scientific papers
SmI2-mediated reduction of α-functionalised amides: Highly enantiospecific access to an atropisomeric amide
Hughes, Adam D.,Simpkins, Nigel S.
, p. 967 - 968 (1998)
SmI2 or SmI2-LiCl mixtures can be used to reduce α-functionalised amides in yields of up to 85% depending upon the amide structure. The method has been applied to the synthesis of an atropisomeric anilide system in highly enantioenriched form, starting with (S)-O-acetyl lactic acid.
Atropisomeric amides: Stereoselective enolate chemistry and enantioselective synthesis via a new SmI2-mediated reduction
Hughes, Adam D.,Price, David A.,Simpkins, Nigel S.
, p. 1295 - 1304 (2007/10/03)
The use of certain types of atropisomeric amides, incorporating an N-MEM-ortho-tert-bityariume group, for stereoselective reactions, has been explored. Enolate reactions of these systems are highly diastereocontrolled, and enantiomerically enriched starting materials can be obtained, starting from lactic acid, via a new SmI2 mediated reduction process.
