Iridium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the generation of axial chiralities

Takanori Shibata; Yoshikazu Arai; Kyoko Takami; Kyoji Tsuchikama; Takayoshi Fujimoto; Satoshi Takebayashi; Kentaro Takagi

doi:10.1002/adsc.200600317

Iridium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the generation of axial chiralities

Takanori Shibata^*, Yoshikazu Arai, Kyoko Takami, Kyoji Tsuchikama, Takayoshi Fujimoto, Satoshi Takebayashi, Kentaro Takagi

^*Corresponding author for this work

School of Advanced Science and Engineering

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

48 Citations (Scopus)

Abstract

A highly enantioselective intermolecular [2 + 2 + 2] cycloaddition of alkynes was catalyzed by a chiral iridium complex. Symmetrical and unsymmetrical diynes, and monoalkynes possessing functional group(s) were subjected to the reaction and various types of axially chiral compounds possessing biaryl skeletons were obtained in good to excellent enantiomeric excesses.

Original language	English
Pages (from-to)	2475-2483
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	348
Issue number	16-17
DOIs	https://doi.org/10.1002/adsc.200600317
Publication status	Published - 2006 Nov

Keywords

Asymmetric catalysis
Chirality
Cycloaddition
Enantioselectivity
Iridium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200600317

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title = "Iridium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the generation of axial chiralities",

abstract = "A highly enantioselective intermolecular [2 + 2 + 2] cycloaddition of alkynes was catalyzed by a chiral iridium complex. Symmetrical and unsymmetrical diynes, and monoalkynes possessing functional group(s) were subjected to the reaction and various types of axially chiral compounds possessing biaryl skeletons were obtained in good to excellent enantiomeric excesses.",

keywords = "Asymmetric catalysis, Chirality, Cycloaddition, Enantioselectivity, Iridium",

author = "Takanori Shibata and Yoshikazu Arai and Kyoko Takami and Kyoji Tsuchikama and Takayoshi Fujimoto and Satoshi Takebayashi and Kentaro Takagi",

year = "2006",

month = nov,

doi = "10.1002/adsc.200600317",

language = "English",

volume = "348",

pages = "2475--2483",

journal = "Advanced Synthesis and Catalysis",

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T1 - Iridium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the generation of axial chiralities

AU - Shibata, Takanori

AU - Arai, Yoshikazu

AU - Takami, Kyoko

AU - Tsuchikama, Kyoji

AU - Fujimoto, Takayoshi

AU - Takebayashi, Satoshi

AU - Takagi, Kentaro

PY - 2006/11

Y1 - 2006/11

N2 - A highly enantioselective intermolecular [2 + 2 + 2] cycloaddition of alkynes was catalyzed by a chiral iridium complex. Symmetrical and unsymmetrical diynes, and monoalkynes possessing functional group(s) were subjected to the reaction and various types of axially chiral compounds possessing biaryl skeletons were obtained in good to excellent enantiomeric excesses.

AB - A highly enantioselective intermolecular [2 + 2 + 2] cycloaddition of alkynes was catalyzed by a chiral iridium complex. Symmetrical and unsymmetrical diynes, and monoalkynes possessing functional group(s) were subjected to the reaction and various types of axially chiral compounds possessing biaryl skeletons were obtained in good to excellent enantiomeric excesses.

KW - Asymmetric catalysis

KW - Chirality

KW - Cycloaddition

KW - Enantioselectivity

KW - Iridium

UR - http://www.scopus.com/inward/record.url?scp=33845270763&partnerID=8YFLogxK

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DO - 10.1002/adsc.200600317

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SN - 1615-4150

VL - 348

SP - 2475

EP - 2483

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 16-17

ER -

Iridium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of diynes and monoalkynes for the generation of axial chiralities

Abstract

Keywords

ASJC Scopus subject areas

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