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Communication | Special issue | Vol 62, No. 1, 2004, pp.223-227
Published online, 14th November, 2003
DOI: 10.3987/COM-03-S(P)62
Enantioenriched Axially Chiral β-Diketimines: Determination of the IAN-amine Barrier to Atropisomerization

Sarah B. Cortright, Ryan A. Yoder, and Jeffrey N. Johnston*

*Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.

Abstract

Enantioenriched (>98% ee) β-diketimines derived from Isoquinoline and 2-Amino Naphthalene (‘IAN-amines’) were prepared. Thermal racemization of a series of R-IAN amines (R = NH2, NHMe, NMe2) revealed a high barrier to atropisomerization (~30 kcal/mol) and its relative insensitivity to substitution at the aminonaphthalene nitrogen. Molecular mechanics calculations accurately predicted the observed relative substituent effects.