103258-06-6Relevant articles and documents
Conformational arm-wrestling: Battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents
Clayden, Jonathan,Foricher, Yann J. Y.,Helliwell, Madeleine,Johnson, Paul,Mitjans, David,Vinader, Victoria
, p. 444 - 454 (2006)
The orientation of a tertiary amide group adjacent to an aromatic ring may be governed by the stereochemistry of an adjacent chiral substituent. With a chiral substituent in both ortho positions, matched/mismatched pairs of isomers result. Evidence for ma
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.