Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

Takanori Shibata; Shiho Yoshida; Yoshikazu Arai; Maiko Otsuka; Kohei Endo

doi:10.1016/j.tet.2007.10.111

Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

Takanori Shibata^*, Shiho Yoshida, Yoshikazu Arai, Maiko Otsuka, Kohei Endo

^*Corresponding author for this work

School of Advanced Science and Engineering

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

52 Citations (Scopus)

Abstract

A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C₂-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C₂-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.

Original language	English
Pages (from-to)	821-830
Number of pages	10
Journal	Tetrahedron
Volume	64
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2007.10.111
Publication status	Published - 2008 Jan 28

Keywords

Axial chirality
Biaryls
Cycloaddition
Enantioselective
Iridium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.10.111

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title = "Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system",

abstract = "A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.",

keywords = "Axial chirality, Biaryls, Cycloaddition, Enantioselective, Iridium",

author = "Takanori Shibata and Shiho Yoshida and Yoshikazu Arai and Maiko Otsuka and Kohei Endo",

note = "Funding Information: We thank Prof. Sentaro Okamoto (Kanagawa University, Japan) for his helpful advice on the synthesis of hexaynes. This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2008",

month = jan,

day = "28",

doi = "10.1016/j.tet.2007.10.111",

language = "English",

volume = "64",

pages = "821--830",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

number = "5",

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T1 - Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

AU - Shibata, Takanori

AU - Yoshida, Shiho

AU - Arai, Yoshikazu

AU - Otsuka, Maiko

AU - Endo, Kohei

N1 - Funding Information: We thank Prof. Sentaro Okamoto (Kanagawa University, Japan) for his helpful advice on the synthesis of hexaynes. This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2008/1/28

Y1 - 2008/1/28

N2 - A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.

AB - A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.

KW - Axial chirality

KW - Biaryls

KW - Cycloaddition

KW - Enantioselective

KW - Iridium

UR - http://www.scopus.com/inward/record.url?scp=37149017176&partnerID=8YFLogxK

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U2 - 10.1016/j.tet.2007.10.111

DO - 10.1016/j.tet.2007.10.111

M3 - Article

AN - SCOPUS:37149017176

SN - 0040-4020

VL - 64

SP - 821

EP - 830

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

Abstract

Keywords

ASJC Scopus subject areas

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