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Communication | Special issue | Vol 99, No. 2, 2019, pp.856-864
Published online, 21st January, 2019
DOI: 10.3987/COM-18-S(F)92
Synthesis and Stereochemical Analysis of Dynamic Planar Chiral Nine-Membered Diallylic Amide: Significant Substituent Effect on Stereochemical Stability

Jun-ichi Hayashi, Kazuhiro Uehara, Yusuke Ano, Yuuya Kawasaki, Kazunobu Igawa, and Katsuhiko Tomooka*

*Department of Molecular and Material Sciences, Institute for Materials Chemistry and Engineering, and IRCCS, Kyushu University, Kasuga, Fukuoka 816-8580, Japan

Abstract

C4-Methyl substituted nine-membered diallylic cyclic amide 1ac was synthesized. HPLC analysis using a chiral stationary phase revealed the presence of isolable enantiomers, whose absolute stereochemistry were determined by X-ray analysis. Studies on the stereochemical stability of 1ac showed that its chirality is more labile than that of the non-substituted congener 1aa and C3-methyl substituted congener 1ab.