Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives

Chu Chun Cheng; Chia Sen Change; Yu Lin Hsu; Ting Yu Lee; Ling Chueh Chang; Shih Hsien Liu; Yao Ting Wu

doi:10.1002/ejoc.200901039

Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives

Chu Chun Cheng, Chia Sen Change, Yu Lin Hsu, Ting Yu Lee, Ling Chueh Chang, Shih Hsien Liu, Yao Ting Wu

Department of Chemistry

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

1 Citation (Scopus)

Abstract

Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7-11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbomene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (M _n) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.

Original language	English
Pages (from-to)	672-679
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	4
DOIs	https://doi.org/10.1002/ejoc.200901039
Publication status	Published - 2010 Jan 29

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives",

abstract = "Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7-11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbomene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (M n) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.",

author = "Cheng, {Chu Chun} and Change, {Chia Sen} and Hsu, {Yu Lin} and Lee, {Ting Yu} and Chang, {Ling Chueh} and Liu, {Shih Hsien} and Wu, {Yao Ting}",

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language = "English",

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T1 - Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives

AU - Cheng, Chu Chun

AU - Change, Chia Sen

AU - Hsu, Yu Lin

AU - Lee, Ting Yu

AU - Chang, Ling Chueh

AU - Liu, Shih Hsien

AU - Wu, Yao Ting

PY - 2010/1/29

Y1 - 2010/1/29

N2 - Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7-11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbomene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (M n) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.

AB - Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7-11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbomene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (M n) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.

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