Journal
ORGANIC LETTERS
Volume 13, Issue 3, Pages 482-485Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102819k
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Funding
- JSPS
- MEXT [B01]
- Grants-in-Aid for Scientific Research [21350020, 21750086] Funding Source: KAKEN
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Conjugate addition of alkylboron compounds (allryl-9-BBN) to imidazol-2-yl alpha,beta-unsaturated ketones proceeded in the presence of a catalytic amount (10 mol %) of CuCl, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes), and t-BuOK. The alkylboranes are available through alkene hydroboration, and thus the overall process represents a reductive conjugate addition of alkenes to enone derivatives. A variety of functional groups are tolerated in both the alkenes and the alpha,beta-unsaturated ketones. The 2-acylimidazole moiety can easily be converted into the corresponding carboxylic acid, ester, and amide derivatives.
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