216155-55-4Relevant academic research and scientific papers
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.
Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon
Clayden, Jonathan,Pink, Jennifer H.,Westlund, Neil,Wilson, Francis X.
, p. 8377 - 8380 (2007/10/03)
By substituting deuterium for hydrogen at positions of high kinetic acidity in amides and carbamates, the usual regiochemical course of their reactions with alkyllithiums (ortholithiation vs. lateral lithiation vs. nucleophilic addition) can be altered or overturned by the kinetic isotope effect. The deuterium substituent functions in these reactions as a protecting group for carbon.
