期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 5, 页码 1398-1408出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo102386s
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资金
- Japan Society for the Promotion of Science (JSPS)
- Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [23790029, 20249002, 21790013] Funding Source: KAKEN
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.
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