600153-18-2Relevant academic research and scientific papers
Synthesis and structural analysis of nine-membered enyne nitrogen heterocycles
Igawa, Kazunobu,Kawabata, Takeshi,Uehara, Kazuhiro,Tomooka, Katsuhiko
, p. 901 - 906 (2015)
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. T
Synthesis and stereochemical analysis of dynamic planar chiral nine-membered diallylic amide: Significant substituent effect on stereochemical stability
Hayashi, Jun-Ichi,Uehara, Kazuhiro,Ano, Yusuke,Kawasaki, Yuuya,Igawa, Kazunobu,Tomooka, Katsuhiko
, p. 856 - 864 (2019/08/01)
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.
Novel synthetic approach to nine-membered diallylic amides: Stereochemical behavior and utility as chiral building block
Tomooka, Katsuhiko,Suzuki, Masaki,Uehara, Kazuhiro,Shimada, Maki,Akiyama, Toshiyuki
scheme or table, p. 2518 - 2522 (2009/04/10)
An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-γ-lycorane using such an optically active amide as a chiral building block. Georg Thieme Verlag Stuttgart.
