Bithiophene with Winding Vine-shaped Molecular Asymmetry. Preparation, Structural Characterization, and Enantioselective Synthesis

被引：9

作者：

Toyomori, Yuka ^{[1
]}

Tsuji, Satoru ^{[1
]}

Mitsuda, Shinobu ^{[1
]}

Okayama, Yoichi ^{[1
]}

Ashida, Shiomi ^{[1
]}

Mori, Atsunori ^{[1
]}

Kobayashi, Toru ^{[2
]}

Miyazaki, Yuji ^{[2
]}

Yaita, Tsuyoshi ^{[2
]}

Arae, Sachie ^{[3
]}

Takahashi, Tamotsu ^{[3
]}

Ogasawara, Masamichi ^{[3
,4
]}

机构：

[1] Kobe Univ, Dept Chem Sci & Engn, Nada Ku, 1-1 Rokkodai, Kobe, Hyogo 6578501, Japan

[2] Japan Atom Energy Agcy, Quantum Beam Sci Directorate, 1-1-1 Koto, Sayo, Hyogo 6795148, Japan

[3] Hokkaido Univ, Inst Catalysis, Kita Ku, Kita21,Nishi10, Sapporo, Hokkaido 0010021, Japan

[4] Univ Tokushima, Grad Sch Sci & Technol, 2-1 Minamijyousanjima Cho, Tokushima 7708506, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2016年 / 89卷 / 12期

关键词：

RING-CLOSING METATHESIS; IMIDO ALKYLIDENE COMPLEXES; REMARKABLY HIGH SOLUBILITY; GENERATED MAGNESIUM AMIDE; TAIL-TYPE OLIGOTHIOPHENES; C-H BOND; OLEFIN-METATHESIS; POLY(3-SUBSTITUTED THIOPHENE)S; 3-SUBSTITUTED THIOPHENES; CONCISE SYNTHESIS;

D O I：

10.1246/bcsj.20160265

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Preparation of 2,2'- bithiophene derivatives bearing omega-alkenyl groups at the 3,3'-positions and ring-closing metathesis reactions of the obtained compound were performed. The reaction of bithiophene bearing 3-butenyl substituents 1 with 5 mol% Grubbs 1st generation catalyst underwent ring-closing metathesis (RCM) to afford the cyclized product 7 showing winding vine-shaped molecular asymmetry in up to 88% yield. Enantio-selective RCM was also achieved by the use of chiral Schrock-Hoveyda molybdenum-alkylidene catalyst in up to 87% ee.

引用

页码：1480 / 1486

页数：7

共 13 条

[1] Bithiophene with winding vine-shaped molecular asymmetry. Preparation, structural characterization, and enantioselective synthesis
1600, Chemical Society of Japan (89):
[2] Double Winding Vine-Shaped Biphenyl with Molecular Asymmetry. Synthesis, Structure, and Properties
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[4] SYNTHESIS OF UNSYMMETRICAL HETEROBIARYLS WITH WINDING VINE-SHAPED MOLECULAR ASYMMETRY THROUGH A CONDENSATION PATHWAY
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[6] Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi’s asymmetric epoxidation
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[7] COMPUTATIONAL STUDIES ON THE RACEMIZATION BARRIERS OF WINDING VINE-SHAPED HETEROBIARYLS WITH MOLECULAR ASYMMETRY
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[8] Synthesis and Racemization Studies of Winding Vine-Shaped Biphenyl Derivatives
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[9] Heterobiaryl as winding-vine shaped molecular asymmetry
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[10] Studies on Diastereoselective Functionalization, Optical Resolution, and Racemization Behaviors of Macrocyclic Bisimidazole of Winding-Vine-Shaped Molecular Asymmetry
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BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (09) : 1331 - 1337

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