Ruthenium-Catalyzed Cascade Reactions of Diynes with Norbornadiene - Synthesis of Norbornene Derivatives

Norbornene 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 diaste...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010-02, Vol.2010 (4), p.672-679
Main Authors: Cheng, Chu-Chun, Chang, Chia-Sen, Hsu, Yu-Lin, Lee, Ting-Yu, Chang, Ling-Chueh, Liu, Shih-Hsien, Wu, Yao-Ting
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Cascade reaction
Chemistry
Cycloaddition
Exact sciences and technology
Norbornadiene
Norbornene
Organic chemistry
Preparations and properties
Ruthenium
Terpenoids
Transfer hydrogenation
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Summary:Norbornene 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 1,7‐diaryl‐1,6‐heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbornene 31 by ring‐opening metathesis polymerization (ROMP). The number‐average molecular weight (Mn) and polymer‐distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively. Norbornene derivatives were prepared from norbornadiene and diynes under the catalysis of Ru complexes. This cascade reaction provided high diastereoselectivity.Additionally, one of these cycloadducts was applied in the synthesis of polynorbornenes by the ring‐opening metathesis polymerization.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200901039