1999年2月3日
Helical chirality induction by point chirality at helix terminal
Journal of the American Chemical Society
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- 巻
- 121
- 号
- 4
- 開始ページ
- 754
- 終了ページ
- 759
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/ja9830849
A series of zinc bilinone derivatives bearing a chiral auxiliary at the helix terminal were prepared to investigate the helical chirality induction in the bilinone framework by the point chirality of the chiral auxiliary. Chiral induction was sensitive to the distance to the asymmetric carbon as well as to substituents on the asymmetric carbon. When the chiral carbon was directly attached to the bilinone 19-oxygen and carried an aromatic group, relatively high helical chirality induction was observed in [19-alkoxy- 2,7,13,18-tetramethyl-3,8,12,17-tetraethyl-1-bilinonato]zinc(II) as demonstrated by variable-temperature 1H NMR and CD studies. The (R)-2- methyl-1-phenylpropanoxy group induced P-helicity in >
95% enantiomeric excess at 223 K in CD2Cl2 (ΔΔG°≥ 6.8 kJ/mol).
95% enantiomeric excess at 223 K in CD2Cl2 (ΔΔG°≥ 6.8 kJ/mol).
- リンク情報
- ID情報
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- DOI : 10.1021/ja9830849
- ISSN : 0002-7863
- SCOPUS ID : 0033518555