Enantioselective Synthesis of Axially Chiral Figure-Eight Spirocycloparaphenylenes via Rh-Catalyzed Intermolecular [2+2+2] Cycloaddition

被引：11

作者：

Wang, Li-Hsiang ^{[1
]}

Nogami, Juntaro ^{[1
]}

Nagashima, Yuki ^{[1
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Tokyo 1528550, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 23期

关键词：

CYCLOTRIMERIZATION;

D O I：

10.1021/acs.orglett.3c00895

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have achieved the enantioselective synthesis of axiallychiralfigure-eight spiro[9.9]-cycloparaphenylene (CPP) tetracarboxylateswith up to 75:25 er via the cationic Rh-(I)/(R)-H-8-BINAP complex-catalyzed chemo-, regio-, and enantioselectiveintermolecular double [2 + 2 + 2] cycloaddition of an achiral symmetrictetrayne with dialkyl acetylenedicarboxylates followed by reductivearomatization. The spiro[9.9]-CPP tetracarboxylates are highly distortedat the phthalate moieties with large dihedral and boat angles andexhibit weak aggregation-induced emission enhancement behavior.

引用

页码：4225 / 4230

页数：6

共 49 条

[1] Strain visualization for strained macrocycles [J].

Colwell, Curtis E. ;

Price, Tavis W. ;

Stauch, Tim ;

Jasti, Ramesh .

CHEMICAL SCIENCE, 2020, 11 (15) :3923-3930

[2] The dynamic, size-dependent properties of [5]-[12]cycloparaphenylenes [J].

Darzi, Evan R. ;

Jasti, Ramesh .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (18) :6401-6410

[3] Synthesis and Chiral Resolution of Twisted Carbon Nanobelts [J].

Fan, Wei ;

Matsuno, Taisuke ;

Han, Yi ;

Wang, Xuhui ;

Zhou, Qifeng ;

Isobe, Hiroyuki ;

Wu, Jishan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (39) :15924-15929

[4] Rhodium-Catalyzed Synthesis, Crystal Structures, and Photophysical Properties of [6]Cycloparaphenylene Tetracarboxylates [J].

Hayase, Norihiko ;

Sugiyama, Haruki ;

Uekusa, Hidehiro ;

Shibata, Yu ;

Tanaka, Ken .

ORGANIC LETTERS, 2019, 21 (11) :3895-3899

[5] Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization [J].

Hayase, Norihiko ;

Miyauchi, Yuta ;

Aida, Yukimasa ;

Sugiyama, Haruki ;

Uekusa, Hidehiro ;

Shibata, Yu ;

Tanaka, Ken .

ORGANIC LETTERS, 2017, 19 (11) :2993-2996

[6] Conjugated Nanohoops Incorporating Donor, Acceptor, Hetero- or Polycyclic Aromatics [J].

Hermann, Mathias ;

Wassy, Daniel ;

Esser, Birgit .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, :15743-15766

[7] Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes [J].

Hitosugi, Shunpei ;

Nakanishi, Waka ;

Yamasaki, Takashi ;

Isobe, Hiroyuki .

NATURE COMMUNICATIONS, 2011, 2

[8] Size-Selective Encapsulation of C60 by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod [J].

Iwamoto, Takahiro ;

Watanabe, Yoshiki ;

Sadahiro, Tatsuya ;

Haino, Takeharu ;

Yamago, Shigeru .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8342-8344

[9] Expanded Helicenes as Synthons for Chiral Macrocyclic Nanocarbons [J].

Kiel, Gavin R. ;

Bay, Katherine L. ;

Samkian, Adrian E. ;

Schuster, Nathaniel J. ;

Lin, Janice B. ;

Handford, Rex C. ;

Nuckolls, Colin ;

Houk, K. N. ;

Tilley, T. Don .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (25) :11084-11091

[10] Cycloparaphenylenes via [2+2+2] cycloaddition [J].

Kohrs, Daniel ;

Volkmann, Jannis ;

Wegner, Hermann A. .

CHEMICAL COMMUNICATIONS, 2022, 58 (54) :7483-7494

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