104264-74-6Relevant academic research and scientific papers
Highly diastereoselective radical reactions of substituted methylideneimidazolidinones and related systems
Adamson, George A.,Beckwith, Athelstan L.J.,Chai, Christina L.L.
, p. 629 - 633 (2007/10/03)
Stannane-mediated radical addition to tnethylideneimidazolidinones occurs with good to excellent diastereo-selectivity. The stereochemical outcome of addition is highly dependent on the nature of the NI substituent on the imidazolidinone ring.
Addition of Chiral Glycine, Methionine, and Vinylglycine enolate Derivatives to Aldehydes and Ketones in the Preparation of Enantiomerically Pure α-Amino-β-hydroxy Acids
Seebach, Dieter,Juaristi, Eusebio,Miller, David D.,Schickli, Christof,Weber, Theodor
, p. 237 - 261 (2007/10/02)
Chiral enolates of imidazolidinones and oxazolidinones from the title amino acids react with carbonyl compounds to afford the corresponding alcohols in excellent yields (see Scheme 5).Furthermore, the addition to aldehydes proceeds with high diastereoselectivity to give, after acid hydrolysis, threo-α-amino-β-hydroxy acids of high enantiomeric purity.Some of the threo-α-amino-β-hydroxy acids prepared in this work are the proteinogenic (S)-threonine (26), the naturally occuring (S)-3-phenylserine (28), and (S)-3-hydroxyleucine (27) as well as the unnatural (S)-4,4,4-rtifluorothreonine (30) and (S)-3-(4-pyridyl)serine (31).The N-methylamide of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (32), the uniqe amino acid in the immunosuppressive cyclosporine, was prepared by the new method.This report presents also information suggesting that both steric and stereoelectronic effects are responsible for the good stereoselectivities observed.
