167777-72-2

Upstream product

• 78183-56-9 (S)-acetoin 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 173069-27-7 Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-prop-(Z)-ylidene]-amine 
• 219701-11-8 (1R,4S)-1-hydroxy-4-<oxy>-1-phenyl-3-pentanone 
• 173069-36-8 (3S,4S)-1-benzyl-4-<(1S)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-hydroxy-4-methylazetidin-2-one 
• 180839-83-2 (3S,4S)-1-Benzyl-3-benzyloxy-4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-azetidin-2-one 
• 173069-39-1 (R)-1-Benzyl-4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-azetidine-2,3-dione 
• 173069-42-6 (R)-3-Benzyl-4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-oxazolidine-2,5-dione 

Relevant academic research and scientific papers

Highly stereoselective epoxidation of α-methyl-γ-hydroxy- α,β-unsaturated esters: Rationalization and synthetic applications

(Chemical Equation Presented) The diastereoselectivity of the nucleophilic epoxidation of γ-hydroxy-α,β-unsaturated esters having a methyl substituent at the α- or β-position was investigated. Epoxidation of the α-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a β-hydroxy-α-methylene- γ-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.