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  1. D400 創薬科学研究科
  2. D400a 雑誌掲載論文
  3. 学術雑誌

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
ACS_catalysis_shibuya_rev2.pdf ACS_catalysis_shibuya_rev2.pdf ファイル公開:2018/04/07 (991.3 kB)
Item type 学術雑誌論文 / Journal Article(1)
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

WEKO 72669

Shibuya, Masatoshi

Search repository
Fujita, Shoji

× Fujita, Shoji

WEKO 72670

Fujita, Shoji

Search repository
Abe, Masanori

× Abe, Masanori

WEKO 72671

Abe, Masanori

Search repository
Yamamoto, Yoshihiko

× Yamamoto, Yoshihiko

WEKO 72672

Yamamoto, Yoshihiko

Search repository
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
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
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