154499-36-2

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 920-46-7 Methacryloyl chloride 

Downstream Products

• 1257664-76-8 (5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-6-(furan-2-yl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-77-9 (5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-6-(fthiophen-2-yl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-74-6 (5R,6R)-6-(3,5-bis(trifluoromethyl)phenyl)-5-((dimethyl(phenyl)silyl)methyl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-71-3 (5R,6R)-6-(3,5-di-tert-butylphenyl)-5-((dimethyl(phenyl)silyl)methyl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-73-5 (5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-6-(4-fluorophenyl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-72-4 (5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-3-((S)-2-hydroxy-1-phenylethyl)-6-(4-methoxyphenyl)-5-methyl-1,3-oxazinane-2,4-dione 
• 1257664-75-7 4-((5R,6R)-5-((dimethyl(phenyl)silyl)methyl)-3-((S)-2-hydroxy-1-phenylethyl)-5-methyl-2,4-dioxo-1,3-oxazinan-6-yl)benzonitrile 
• 154499-37-3 (4S)-3-<(2R)-methyl-5-hexenoyl>-4-phenyl-2-oxazolidinone 

Relevant academic research and scientific papers

Copper-catalysed domino silylative aldol reaction leading to stereocontrolled chiral quaternary carbons

(Chemical Equation Presented) Asymmetric aldol reaction: A domino silylation-aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl.

Palladium(II)-Catalyzed Asymmetric Acetalization of Alkenes

The terminal olefinic carbon of N-methaacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdCl2 catalyst.The use of 4(S)-isopropyl-, phenyl-, and tert-butyl-2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'S)-acetals in 61, 80, and 95percent de, respectively.Reductive removal of the auxiliary with LiAlH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal.The enantiomer of this compound, derived from 4(R)-substituted oxazolidinones, served as a building block for synthesizing a 1β-methylcarbapenem precursor in high enantiomeric excess.In the acetalization of 3',3'-dideuteriated methacryloyl-4-isopropyloxazolidinone with MeOH, one D-atom on the terminal olefinic carbon stereoselectively migrated to the chiral center in the product acetal.On the basis of this 1,2-hydride migration and the conformational preference of the methacryloyl moiety, the reaction pathway and the mechanism of the diastereoselection are discussed.