134577-01-8

Upstream product

• 114341-77-4 α-bromopropionyl 2-oxazolidinone amide 
• 100-52-7 benzaldehyde 
• 60420-27-1 N-propionyloxazolidin-2-one 
• 116836-48-7 syn-3-(3-hydroxy-2-methyl-3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 99114-33-7 anti-3-(3-hydroxy-2-methyl-3-phenylpropanoyl)-1,3-oxazolidin-2-one 

Downstream Products

• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 637337-86-1 (E)-N-(2-hydroxyethyl)-2-methyl-3-phenyl-2-propenamide 

Relevant academic research and scientific papers

Stereoselective rearrangement of β-hydroxy-N-acyloxazolidin-2-ones to afford N-2-hydroxyethyl-1,3-oxazinane-2,4-diones

Zinc alkoxides of syn- or anti-β-hydroxy-N-acyloxazolidin-2-ones undergo stereoselective rearrangement to afford their corresponding syn- or anti-N-2-hydroxyethyl-1,3-oxazinane-2,4-diones in good yield.

Stereoselective synthesis of (E)-trisubstituted α,β-unsaturated amides and acids

Potassium alkoxides of N-acyl-oxazolidin-2-one-syn-aldols undergo stereoselective elimination reactions to afford a range of trisubstituted (E)-αβ-unsaturated amides in >95% de, that may be subsequently converted into their corresponding (E)-αβ-unsaturated acids or (E)-αβ-unsaturated oxazolines in good yield. syn-Aldols derived from αβ-unsaturated aldehydes gave their corresponding trisubstituted (E)-αβ-unsaturated-amides with poorer levels of diastereocontrol, whilst there was a similar loss in (E)-selectivity during elimination of syn-aldols derived from chiral aldehydes. These elimination reactions proceed via rearrangement of the potassium alkoxide of the syn-aldol to a 1,3-oxazinane-2,4-dione enolate intermediate that subsequently eliminates carbon dioxide to afford a trisubstituted (E)-αβ-unsaturated amide. The (E)-selectivity observed during the ElcB-type elimination step has been rationalised using a simple conformational model that employs a chair-like transition state to explain the observed stereocontrol. The Royal Society of Chemistry 2005.

HIGHLY STEREOSELECTIVE REFORMATSKY REACTIONS OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES WITH VARIOUS ALDEHYDES

The Reformatsky reactions of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities.The highest 2,3-syn-diastereoselect