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Communication | Special issue | Vol 90, No. 2, 2015, pp.901-906
Published online, 19th September, 2014
DOI: 10.3987/COM-14-S(K)109
■ Synthesis and Structural Analysis of Nine-Membered Enyne Nitrogen Heterocycles

Kazunobu Igawa, Takeshi Kawabata, Kazuhiro Uehara, and Katsuhiko Tomooka*

*Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan

Abstract

An efficient approach to the nine-membered enyne nitrogen heterocycle 3 is presented. 1H NMR analysis reveals that both 3a (R = H, X = Ts) and 3b (R = Me, X = Ts) exhibit significant labile planar chirality in solution at ambient temperature. The X-ray analysis of 3b shows that the enantiotopic faces of the alkene are differentiated by the alkyne moiety in the solid state.