85630-26-8Relevant academic research and scientific papers
Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation
Miah, M. A. Jalil,Sibi, Mukund P.,Chattopadhyay,Familoni, Oluwole B.,Snieckus, Victor
, p. 447 - 454 (2017/12/15)
A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the
Atropisomeric benzamides and naphthamides as chiral auxiliaries
Clayden, Jonathan,Helliwell, Madeleine,McCarthy, Catherine,Westlund, Neil
, p. 3232 - 3249 (2007/10/03)
Atropisomeric compounds whose chirality resides in a rotationally restricted aryl-CONR2 bond may be employed as chiral auxiliaries. The electron-withdrawing amide group causes problems in the diastereoselective functionalisation of enolates derived from atropisomeric phenyl esters, but a strategy based on atroposelective nucleophilic addition to a chiral aldehyde followed by stereospecific [3,3] sigmatropic rearrangement allows atropisomeric naphthamides to be used as auxiliaries. The auxiliaries are resolved by dynamic resolution during aminal formation using a proline-derived diamine. The Royal Society of Chemistry 2000.
The Directed Ortho Lithiation of O-Aryl Carbamates. An Anionic Equivalent of the Fries Rearrangement
Sibi, Mukund P.,Snieckus, Victor
, p. 1935 - 1937 (2007/10/02)
Ortho-Lithiated O-aryl carbamates 3 constitute new synthetic intermediates which by treatment with a variety of electrophiles lead to ortho-substituted carbamates 4 and by rearrangement provide salicylamides 6.
