Catalytic enantioselective synthesis of chiral tetraphenylenes: Consecutive inter- and intramolecular cycloadditions of two triynes

Takanori Shibata; Tatsuya Chiba; Hiroyuki Hirashima; Yasunori Ueno; Kohei Endo

doi:10.1002/anie.200903715

Catalytic enantioselective synthesis of chiral tetraphenylenes: Consecutive inter- and intramolecular cycloadditions of two triynes

Takanori Shibata^*, Tatsuya Chiba, Hiroyuki Hirashima, Yasunori Ueno, Kohei Endo

^*Corresponding author for this work

School of Advanced Science and Engineering

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

57 Citations (Scopus)

Abstract

Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO₂Me) ₂, O).

Original language	English
Pages (from-to)	8066-8069
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	43
DOIs	https://doi.org/10.1002/anie.200903715
Publication status	Published - 2009 Oct 12

Keywords

Alkynes
Asymmetric synthesis
Chirality
Cycloaddition
Rhodium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200903715

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abstract = "Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO2Me) 2, O).",

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AU - Hirashima, Hiroyuki

AU - Ueno, Yasunori

AU - Endo, Kohei

PY - 2009/10/12

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N2 - Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO2Me) 2, O).

AB - Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO2Me) 2, O).

KW - Alkynes

KW - Asymmetric synthesis

KW - Chirality

KW - Cycloaddition

KW - Rhodium

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Catalytic enantioselective synthesis of chiral tetraphenylenes: Consecutive inter- and intramolecular cycloadditions of two triynes

Abstract

Keywords

ASJC Scopus subject areas

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