220208-74-2

Upstream product

• 106-95-6 allyl bromide 
• 220208-72-0 2-(hydroxymethyl)-N,N-diisopropylbenzamide 
• 103258-06-6 2-formyl-N,N-diisopropylbenzamide 
• 20383-28-2 N,N-diisopropyl benzamide 

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.

Enantioselective [2,3]-Wittig rearrangement via sparteine-mediated lateral metalation of N,N-dialkyl-o-allyloxymethylbenzamides and o-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. With N,N-diethyl-o-allyloxymethylbenzamide, enantiomeric excess up to 60% was observed in pentane. These results suggest that the carbamoyl group can effectively assist the transfer of stereoinformation by coordinating with the (-)-sparteine-n-BuLi complex. Other functional groups (OMe, OCONR2, OMOM, F) were impotent to the enantiodifferentiation of this rearrangement.