220208-72-0Relevant academic research and scientific papers
Phthalide: A direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides
McNulty, James,Keskar, Kunal
supporting information, p. 2404 - 2407 (2013/06/05)
The direct synthesis of new hemilabile ligands from the economical, readily available lactone phthalide is described. Pd-complexes of one such ligand were found highly effective in general Suzuki-Miyaura cross-coupling reactions, including deactivated and hindered aryl chlorides. The Royal Society of Chemistry 2013.
Sparteine-mediated enantioselective [2,3]-Wittig rearrangement of allyl ortho-substituted benzyl ethers and ortho-substituted benzyl prenyl ethers
Kawasaki, Takeshi,Kimachi, Tetsutaro
, p. 6847 - 6862 (2007/10/03)
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
Kawasaki, Takeshi,Kimachi, Tetsutaro
, p. 1429 - 1431 (2007/10/03)
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.
