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Shibata K, Kimura M, Shimizu M, et al. Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde. Org Lett. 2001;3(14):2181-3doi: 10.1021/ol0100879.
Shibata, K., Kimura, M., Shimizu, M., & Tamaru, Y. (2001). Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde. Organic letters, 3(14), 2181-3. https://doi.org/10.1021/ol0100879
Shibata, K, et al. "Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde." Organic letters vol. 3,14 (2001): 2181-3. doi: https://doi.org/10.1021/ol0100879
Shibata K, Kimura M, Shimizu M, Tamaru Y. Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde. Org Lett. 2001 Jul 12;3(14):2181-3. doi: 10.1021/ol0100879. PMID: 11440574.
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Org Lett. 2001 Jul 12;3(14):2181-3. doi: 10.1021/ol0100879.

Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde.

Organic letters

K Shibata, M Kimura, M Shimizu, Y Tamaru

Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.

PMID: 11440574 DOI: 10.1021/ol0100879

Abstract

[reaction: see text] In the presence of a catalytic amount of Ni(acac)(2), Et(3)B and Et(2)Zn nicely promote a reductive homoallylic cyclization of omega-dienyl aldehydes and provide 2-allylcyclopentanols and -cyclohexanols with high stereoselectivity in excellent yield. The reaction requires only two kinds of commercially available, inexpensive reagents, Ni(acac)(2) and Et(2)Zn or Et(3)B, and completes at room temperature within 30 min with Et(2)Zn and 1-2 days with Et(3)B. No ligand additives (e.g., phosphine, nitrogen compounds) are required.

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