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Brønsted Acid/Silane Catalytic System for Intramolecular Hydroalkoxylation and Hydroamination of Unactivated Alkynes
http://hdl.handle.net/2237/26769
b83ac7ee-f750-4227-8209-48698a655d41
名前 / ファイル | ライセンス | アクション | |
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2017-07-05 | |||||
タイトル | ||||||
タイトル | Brønsted Acid/Silane Catalytic System for Intramolecular Hydroalkoxylation and Hydroamination of Unactivated Alkynes | |||||
著者 |
Shibuya, Masatoshi
× Shibuya, Masatoshi× Fujita, Shoji× Abe, Masanori× Yamamoto, Yoshihiko |
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権利 | ||||||
権利情報 | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in [ACS Catalysis], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [http://pubs.acs.org/articlesonrequest/AOR-ccnW7GCz94tz5qnyYxff].” | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | alkyne | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Brønsted acid | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | electrophilic activation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | hydroalkoxylation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | hydroamination | |||||
抄録 | ||||||
内容記述 | The Brønsted acid-catalyzed intramolecular hydroalkoxylation and hydroamination of unactivated alkynes are described. We found that unactivated alkynes are electrophilically activated by a catalytic amount of bis(trifluoromethanesulfonyl)imide to undergo intramolecular hydroalkoxylation and hydroamination. In the presence of silane, the formed reactive exo-cyclic enol ether and exo-cyclic enamine intermediates are effectively reduced to the corresponding saturated cyclic ethers and N-protected cyclic amines. The 2,4-cis and 2,5-cis pyrrolidine derivatives are produced with high diastereoselectivity. Taking advantage of this selectivity, the 2,5-cis-disubstituted prolinol was also synthesized from glutamic acid in the optically active form. | |||||
内容記述タイプ | Abstract | |||||
出版者 | ||||||
出版者 | ACS Publications | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプresource | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | journal article | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 2155-5435 | |||||
書誌情報 |
ACS Catalysis 巻 7, 号 4, p. 2848-2852, 発行日 2017-04-07 |
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著者版フラグ | ||||||
値 | author | |||||
URI | ||||||
識別子 | http://hdl.handle.net/2237/26769 | |||||
識別子タイプ | HDL | |||||
URI | ||||||
識別子 | http://dx.doi.org/10.1021/acscatal.7b00403 | |||||
識別子タイプ | DOI |