Enantioenriched axially chiral beta-diketimines:determinatino of the ian-amine barrier to atropisomerization

摘要

Enantioenriched (>98% ee)beta-diketimines derived from Isoquinoline and 2-SAmino Naphthalene ('IAN-amines')were prepared.Thermal recemization of a series of R-IAN amines (R=NH_2,NHMe,NMe_2)revealed a high barrier to atropisomerization (~30 kcal/mol)and its relative insensitivityito substitution at hte aminonaphthalene nitrogen.Molecular mechanics calculations accurately predicted the observed relative substitutent effects.