233589-46-3

Upstream product

• 233589-44-1 (S)-N-isopropyl-o-(1-hydroxy-3-butenyl)benzamide 
• 233589-43-0 N-isopropyl-o-allyloxymethylbenzamide 
• 24282-29-9 (S)-3-allylisobenzofuran-1(3H)-one 
• 220208-77-5 (S)-N,N-diethyl-o-(1-hydroxy-3-butenyl)benzamide 
• 5440-69-7 N-isopropylbenzamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 233589-45-2 (S)-3-(2-hydroxyethyl)phthalide 

Relevant academic research and scientific papers

Sparteine-mediated enantioselective [2,3]-Wittig rearrangement of allyl ortho-substituted benzyl ethers and ortho-substituted benzyl prenyl ethers

The (-)-sparteine-mediated enantioselective [2,3]-Wittig rearrangement of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers has been investigated. Enantiomeric excess up to 60% was observed as for the reaction with N,N-diethyl-o-allyloxymetylbenzamide. From the mechanistic investigations, it was suggested that the stereoinformation was introduced at the deprotonation step. Substoichiometric amount of (-)- sparteine (0.2 equiv.) did not decrease the enantioselectivity. Introduction of functional groups other than carbamoyl group did not enhance the enantioselectivity in this rearrangement.