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Synthesis of γ,δ-Unsaturated Esters and Amides via Au(I)-Catalyzed Reactions of Aryl Ynol Ethers or Ynamides with Allylic Alcohols
| Title: | Synthesis of γ,δ-Unsaturated Esters and Amides via Au(I)-Catalyzed Reactions of Aryl Ynol Ethers or Ynamides with Allylic Alcohols |
| Authors: | Misawa, Souta Browse this author | | Miyairi, Asaki Browse this author | | Oonishi, Yoshihiro Browse this author →KAKEN DB | | Nolan, Steven P. Browse this author | | Sato, Yoshihiro Browse this author →KAKEN DB |
| Keywords: | gold catalysis | | ynols | | ynamides | | hydroalkoxylation | | Claisen rearrangement | | esters | | amides |
| Issue Date: | 29-Sep-2021 |
| Publisher: | Georg Thieme Verlag |
| Journal Title: | Synthesis-stuttgart |
| Volume: | 53 |
| Issue: | 24 |
| Start Page: | 4644 |
| End Page: | 4653 |
| Publisher DOI: | 10.1055/a-1559-3020 |
| Abstract: | Polarized alkynes such as ynol ethers and ynamides have attracted much attention due to their inherent unique reactivity. Herein, we report Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reactions of aryl ynol ethers and ynamides with allylic alcohols. At the first stage (hydroalkoxylation) of this cascade reaction, attack of allylic alcohols to aryl ynol ethers or ynamides occurs at the alpha-position of the polarized alkynes in a completely regioselective manner. Claisen rearrangement of the resulting adducts subsequently takes place to give gamma,delta-unsaturated esters or amides, respectively. The [Au(IPr)NTf (2)] catalyst is most effective for this reaction, and the reaction proceeds under mild conditions (in the case of aryl ynol ether: in THF, 60 degrees C; in the case of ynamides: in toluene, 80 degrees C) in an atom-economical way. |
| Rights: | This is an Accepted Manuscript of an article published by Thieme Publishing Group in Journal Title on Publication Date, available online at https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1559-3020 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/86987 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 大西 英博
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