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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Chiral N-heterocyclic carbene-copper(I)-catalyzed asymmetric allylic arylation of aliphatic allylic bromides: Steric and electronic effects on γ-selectivity
Journal of Organic Chemistry, Volume 76, No. 5, Year 2011
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Description
Chiral N-heterocyclic carbene ligands were electronically and sterically tuned to improve γ-selectivity in copper(I)-catalyzed asymmetric allylic arylation of aliphatic allylic bromides with several aryl Grignard reagents. High γ-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 carbene ligand or allylic bromide was bulky. The results indicated that electron deficiency and steric hindrance of the initially formed σ-allyl copper intermediate enhance the rate of the reductive elimination to give γ-products as major isomers.(Figure Presented) © 2011 American Chemical Society.
Authors & Co-Authors
Selim, Khalid B.
Egypt, Mansoura
Faculty of Pharmacy
Nakanishi, Hirotsugu
Japan, Kyoto
Kyoto University
Matsumoto, Yasumasa
Japan, Kyoto
Kyoto University
Yamamoto, Yasutomo
Japan, Kyotanabe
Doshisha Women's College of Liberal Arts
Yamada, Ken Ichi
Japan, Kyoto
Kyoto University
Tomioka, Kiyoshi
Japan, Kyoto
Kyoto University
Japan, Kyotanabe
Doshisha Women's College of Liberal Arts
Statistics
Citations: 48
Authors: 6
Affiliations: 3
Identifiers
Doi:
10.1021/jo102386s
ISSN:
00223263
e-ISSN:
15206904