MISC

2002年11月

Copper(I) tert-butoxide-promoted 1,4 C-sp2-to-O silyl migration: Generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides

JOURNAL OF ORGANIC CHEMISTRY
  • H Taguchi
  • ,
  • K Ghoroku
  • ,
  • M Tadaki
  • ,
  • A Tsubouchi
  • ,
  • T Takeda

67
24
開始ページ
8450
終了ページ
8456
記述言語
英語
掲載種別
DOI
10.1021/jo025973r
出版者・発行元
AMER CHEMICAL SOC

Successive treatment of the (Z)-gamma-trimethylsilyl allylic alcohols with copper(I) tert-butoxide and allylic halides followed by the tetrabutylammonium fluoride-assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration. Similar treatment of the organometallic intermediates with aryl and vinylic halides in the presence of palladium(0) catalyst gave the corresponding cross-coupling products in good yields. The stereoselective preparation of the starting materials is also described.

リンク情報
DOI
https://doi.org/10.1021/jo025973r
CiNii Articles
http://ci.nii.ac.jp/naid/80015660919
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/12444624
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000179509400020&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/jo025973r
  • ISSN : 0022-3263
  • CiNii Articles ID : 80015660919
  • PubMed ID : 12444624
  • Web of Science ID : WOS:000179509400020

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