Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene

Ryo Irie; Akihiro Tanoue; Suguru Urakawa; Tatsushi Imahori; Kazunobu Igawa; Taisuke Matsumoto; Katsuhiko Tomooka; Shinsuke Kikuta; Tatsuya Uchida; Tsutomu Katsuki

doi:10.1246/cl.2011.1343

Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene

Ryo Irie, Akihiro Tanoue, Suguru Urakawa, Tatsushi Imahori, Kazunobu Igawa, Taisuke Matsumoto, Katsuhiko Tomooka, Shinsuke Kikuta, Tatsuya Uchida, Tsutomu Katsuki

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

25 Citations (Scopus)

Abstract

A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed.

Original language	English
Pages (from-to)	1343-1345
Number of pages	3
Journal	Chemistry Letters
Volume	40
Issue number	12
DOIs	https://doi.org/10.1246/cl.2011.1343
Publication status	Published - 2011

All Science Journal Classification (ASJC) codes

Chemistry(all)

Access to Document

10.1246/cl.2011.1343

Cite this

@article{96231f072574499e9a1a4e9ec04a0d07,

title = "Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene",

abstract = "A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed.",

author = "Ryo Irie and Akihiro Tanoue and Suguru Urakawa and Tatsushi Imahori and Kazunobu Igawa and Taisuke Matsumoto and Katsuhiko Tomooka and Shinsuke Kikuta and Tatsuya Uchida and Tsutomu Katsuki",

year = "2011",

doi = "10.1246/cl.2011.1343",

language = "English",

volume = "40",

pages = "1343--1345",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "The Chemical Society of Japan",

number = "12",

}

TY - JOUR

T1 - Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene

AU - Irie, Ryo

AU - Tanoue, Akihiro

AU - Urakawa, Suguru

AU - Imahori, Tatsushi

AU - Igawa, Kazunobu

AU - Matsumoto, Taisuke

AU - Tomooka, Katsuhiko

AU - Kikuta, Shinsuke

AU - Uchida, Tatsuya

AU - Katsuki, Tsutomu

PY - 2011

Y1 - 2011

N2 - A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed.

AB - A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed.

UR - http://www.scopus.com/inward/record.url?scp=82155167404&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=82155167404&partnerID=8YFLogxK

U2 - 10.1246/cl.2011.1343

DO - 10.1246/cl.2011.1343

M3 - Article

AN - SCOPUS:82155167404

SN - 0366-7022

VL - 40

SP - 1343

EP - 1345

JO - Chemistry Letters

JF - Chemistry Letters

IS - 12

ER -

Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this