論文

2011年3月

Chiral N-Heterocyclic Carbene-Copper(I)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides: Steric and Electronic Effects on gamma-Selectivity

JOURNAL OF ORGANIC CHEMISTRY
  • Khalid B. Selim
  • ,
  • Hirotsugu Nakanishi
  • ,
  • Yasumasa Matsumoto
  • ,
  • Yasutomo Yamamoto
  • ,
  • Ken-ichi Yamada
  • ,
  • Kiyoshi Tomioka

76
5
開始ページ
1398
終了ページ
1408
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1021/jo102386s
出版者・発行元
AMER CHEMICAL SOC

Chiral N-heterocyclic carbene ligands were electronically and sterically tuned to improve gamma-selectivity in copper(I)-catalyzed asymmetric allylic arylation of aliphatic allylic bromides with several aryl Grignard reagents. High gamma-selectivity was realized when either the aryl group of the Grignard reagent or the aryl group on the N-substituent of the carbene ligand was electron-deficient or when either the car bene ligand or allylic bromide was bulky. The results indicated that electron deficiency and steric hindrance of the initially formed sigma-allyl copper intermediate enhance the rate of the reductive elimination to give gamma-products as major isomers.

リンク情報
DOI
https://doi.org/10.1021/jo102386s
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000287636200020&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/jo102386s
  • ISSN : 0022-3263
  • eISSN : 1520-6904
  • Web of Science ID : WOS:000287636200020

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