Helical chirality induction by point chirality at helix terminal

被引:61
作者
Mizutani, T [1 ]
Yagi, S
Morinaga, T
Nomura, T
Takagishi, T
Kitagawa, S
Ogoshi, H
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Sakyo Ku, Kyoto 6068501, Japan
[2] Univ Osaka Prefecture, Dept Appl Mat Sci, Sakai, Osaka 5998531, Japan
[3] Fukui Natl Coll Technol, Fukui 9160064, Japan
关键词
D O I
10.1021/ja9830849
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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-tetraethyl-3,8,12,17-tetraethyl-1-bilinonato]zinc(II as demonstrated by variable-temperature H-1 NMR and CD studies. The (R)-2-methyl-1-phenylpropanoxy group induced P-helicity in > 95 % enantiomeric excess at 223 K in CD2Cl2 (Delta Delta G degrees greater than or equal to 6.8 kJ/mol).
引用
收藏
页码:754 / 759
页数:6
相关论文
共 33 条