Synthesis and Stereochemical Properties of Chiral Hetero[7]helicenes Structured by a Benzodiheterole Ring Core

被引：9

作者：

Arae, Sachie ^{[1
]}

Mori, Takaaki ^{[1
]}

Kawatsu, Takahiro ^{[1
]}

Ueda, Daiki ^{[1
]}

Shigeta, Yusuke ^{[1
]}

Hamamoto, Nobutsugu ^{[1
]}

Fujimoto, Hitoshi ^{[1
]}

Sumimoto, Michinori ^{[2
]}

Imahori, Tatsushi ^{[3
]}

Igawa, Kazunobu ^{[4
]}

Tomooka, Katsuhiko ^{[4
]}

Punniyamurthy, Tharmalingam ^{[5
]}

Irie, Ryo ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Adv Sci & Technol, Dept Chem, Chuo Ku, 2-39-1 Kurokami, Kumamoto 8608555, Japan

[2] Yamaguchi Univ, Grad Sch Sci & Technol Innovat, Ube, Yamaguchi 7558611, Japan

[3] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjyuku Ku, 1-3 Kagurazaka, Tokyo 1628601, Japan

[4] Kyushu Univ, Inst Mat Chem & Engn, 6-1 Kasuga Koen, Kasuga, Fukuoka 8168580, Japan

[5] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

CHEMISTRY LETTERS | 2017年 / 46卷 / 08期

关键词：

Heterohelicene; Benzodiheterole; Domino cyclodehydrogenation; ONE HUNDRED YEARS; RUTHENIUM-CATALYZED AROMATIZATION; ENANTIOSELECTIVE GOLD-CATALYSIS; PHENOLIC HYDROXY FUNCTIONS; CASCADE CYCLIZATION; CRYSTAL-STRUCTURE; STEREOSELECTIVE SYNTHESES; SUBSTITUTED NAPHTHALENES; NUCLEOPHILIC ADDITIONS; ENEDIYNES;

D O I：

10.1246/cl.170410

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new hetero[7]helicene 1(NN) structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)(2) and O-2 as the key step. Significantly, 1(NN) was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1(NN) and DFT calculations on its variants revealed that the stereochemical stability of the benzodiheterole-based helicenes was highly dependent on not only the heteroaromatic ring component but also on the N-substituent of the pyrrole ring unit.

引用

页码：1214 / 1216

页数：3

共 73 条

[51] Novel synthesis of oxa[9]helicenes by Lawesson's reagent-mediated cyclization of helical quinone derivatives [J].