Enantioselective synthesis of chiral tripodal cage compounds by [2 + 2 + 2] cycloaddition of branched triynes

Takanori Shibata; Toshifumi Uchiyama; Kohei Endo

doi:10.1021/ol9014893

Enantioselective synthesis of chiral tripodal cage compounds by [2 + 2 + 2] cycloaddition of branched triynes

Takanori Shibata^*, Toshifumi Uchiyama, Kohei Endo

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

49 被引用数 (Scopus)

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Cyclotrimerization of triynes branched by a nitrogen atom of 2-aminophenol yielded planar-chiral tripodal cage compounds. When a cationic Rh-Me-DUPHOS catalyst was used, the cycloadducts were obtained in high yield and excellent ee, and a macrocyclic compound with a [15]cyclophane system was also obtained. This method can be further applied to the synthesis of a triarmed pyridinophane by the intramolecular reaction of a diyne-nitrile.

本文言語	English
ページ（範囲）	3906-3908
ページ数	3
ジャーナル	Organic Letters
巻	11
号	17
DOI	https://doi.org/10.1021/ol9014893
出版ステータス	Published - 2009 9月 3

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol9014893

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AU - Shibata, Takanori

AU - Uchiyama, Toshifumi

AU - Endo, Kohei

PY - 2009/9/3

Y1 - 2009/9/3

N2 - Cyclotrimerization of triynes branched by a nitrogen atom of 2-aminophenol yielded planar-chiral tripodal cage compounds. When a cationic Rh-Me-DUPHOS catalyst was used, the cycloadducts were obtained in high yield and excellent ee, and a macrocyclic compound with a [15]cyclophane system was also obtained. This method can be further applied to the synthesis of a triarmed pyridinophane by the intramolecular reaction of a diyne-nitrile.

AB - Cyclotrimerization of triynes branched by a nitrogen atom of 2-aminophenol yielded planar-chiral tripodal cage compounds. When a cationic Rh-Me-DUPHOS catalyst was used, the cycloadducts were obtained in high yield and excellent ee, and a macrocyclic compound with a [15]cyclophane system was also obtained. This method can be further applied to the synthesis of a triarmed pyridinophane by the intramolecular reaction of a diyne-nitrile.

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Enantioselective synthesis of chiral tripodal cage compounds by [2 + 2 + 2] cycloaddition of branched triynes

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