254756-13-3Relevant academic research and scientific papers
Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides
Clayden, Jonathan,Westlund, Neil,Frampton, Christopher S.
, p. 1379 - 1385 (2000)
Restricted rotation about the Ar-CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-1-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisation, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.
Diastereoisomeric atropisomers of peri-substituted naphthamides: Synthesis, stereoselectivity and stability
Clayden, Jonathan,Westlund, Neil,Wilson, Francis X.
, p. 7883 - 7887 (2007/10/03)
8-Formyl-1-naphthamides can be made by perilithiation of 1-(dimethylaminomethyl)-naphthalene, quenching the organolithium with a carbamoyl chloride and subjecting the product amine to a Polonovski reaction. The naphthamides react stereoselectively with nucleophiles to give predominantly the syn atropisomers of the product alcohols. Oxidation gives ketones which also give mainly the syn atropisomer on reduction. The rate of thermal epimerisation of the products is high relative to 2-substituted 1-naphthamides: the barrier to Ar-CO rotation is ca. 90 kJ mol-1.
