Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core

Sachie Arae; Takaaki Mori; Takahiro Kawatsu; Daiki Ueda; Yusuke Shigeta; Nobutsugu Hamamoto; Hitoshi Fujimoto; Michinori Sumimoto; Tatsushi Imahori; Kazunobu Igawa; Katsuhiko Tomooka; Tharmalingam Punniyamurthy; Ryo Irie

doi:10.1246/cl.170410

Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core

Sachie Arae, Takaaki Mori, Takahiro Kawatsu, Daiki Ueda, Yusuke Shigeta, Nobutsugu Hamamoto, Hitoshi Fujimoto, Michinori Sumimoto, Tatsushi Imahori, Kazunobu Igawa, Katsuhiko Tomooka, Tharmalingam Punniyamurthy, Ryo Irie

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

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 O₂ 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 stereo-chemical 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.

Original language	English
Pages (from-to)	1214-1216
Number of pages	3
Journal	Chemistry Letters
Volume	46
Issue number	8
DOIs	https://doi.org/10.1246/cl.170410
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.170410

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title = "Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core",

abstract = "A new hetero[7]helicene 1NN structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)2 and O2 as the key step. Significantly, 1NN was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1NN and DFT calculations on its variants revealed that the stereo-chemical 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.",

author = "Sachie Arae and Takaaki Mori and Takahiro Kawatsu and Daiki Ueda and Yusuke Shigeta and Nobutsugu Hamamoto and Hitoshi Fujimoto and Michinori Sumimoto and Tatsushi Imahori and Kazunobu Igawa and Katsuhiko Tomooka and Tharmalingam Punniyamurthy and Ryo Irie",

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doi = "10.1246/cl.170410",

language = "English",

volume = "46",

pages = "1214--1216",

journal = "Chemistry Letters",

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publisher = "The Chemical Society of Japan",

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TY - JOUR

T1 - Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core

AU - Arae, Sachie

AU - Mori, Takaaki

AU - Kawatsu, Takahiro

AU - Ueda, Daiki

AU - Shigeta, Yusuke

AU - Hamamoto, Nobutsugu

AU - Fujimoto, Hitoshi

AU - Sumimoto, Michinori

AU - Imahori, Tatsushi

AU - Igawa, Kazunobu

AU - Tomooka, Katsuhiko

AU - Punniyamurthy, Tharmalingam

AU - Irie, Ryo

PY - 2017

Y1 - 2017

N2 - A new hetero[7]helicene 1NN structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)2 and O2 as the key step. Significantly, 1NN was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1NN and DFT calculations on its variants revealed that the stereo-chemical 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.

AB - A new hetero[7]helicene 1NN structured by a diazabenzodiheterole (pyrroloindole) ring core was successfully synthesized by catalytic domino cyclodehydrogenation with Pd(OAc)2 and O2 as the key step. Significantly, 1NN was stereochemically stable at room temperature and could be subjected to optical resolution by chiral HPLC. Furthermore, kinetic analysis of 1NN and DFT calculations on its variants revealed that the stereo-chemical 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.

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DO - 10.1246/cl.170410

M3 - Article

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SN - 0366-7022

VL - 46

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EP - 1216

JO - Chemistry Letters

JF - Chemistry Letters

IS - 8

ER -

Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core

Abstract

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