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
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- 巻
- 76
- 号
- 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
- ID情報
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- DOI : 10.1021/jo102386s
- ISSN : 0022-3263
- eISSN : 1520-6904
- Web of Science ID : WOS:000287636200020