144561-93-3Relevant articles and documents
Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters
Li, Jia-Qi,Quan, Xu,Andersson, Pher G.
, p. 10609 - 10616 (2012/11/07)
α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright
Asymmetric aldol and alkylation reactions mediated by the 'quat' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone
Davies,Doisneau,Prodger,Sanganee
, p. 2373 - 2376 (2007/10/02)
Enolates derived from the N-propionoyl derivative of the 'quat' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone undergo highly stereoselective aldol and alkylation reactions. Removal of the auxiliary has been demonstrated with LiOH, PhCH2OLi, MeOMgBr and LiAlH4 to generate respectively (2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid in homochiral form, and with 96% e.e. (S)-2-methyl-3-phenylpropionic acid and derived methyl and benzyl esters and with >94% e.e. (S)-2-methyl-3-phenylpropanol.