Display options
Cite
Huang K, Wang H, Liu L, et al. Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry. 2016;22(19):6458-65doi: 10.1002/chem.201600248.
Huang, K., Wang, H., Liu, L., Chang, W., & Li, J. (2016). Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry (Weinheim an der Bergstrasse, Germany), 22(19), 6458-65. https://doi.org/10.1002/chem.201600248
Huang, Kaimeng, et al. "Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,19 (2016): 6458-65. doi: https://doi.org/10.1002/chem.201600248
Huang K, Wang H, Liu L, Chang W, Li J. Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry. 2016 May 04;22(19):6458-65. doi: 10.1002/chem.201600248. Epub 2016 Mar 22. PMID: 26946315.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2016 May 04;22(19):6458-65. doi: 10.1002/chem.201600248. Epub 2016 Mar 22.

Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kaimeng Huang, Hongkai Wang, Lingyan Liu, Weixing Chang, Jing Li

Affiliations

  1. The College of Chemistry, the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Wiejin Road 94#, Tianjin, 300071, P. R. China.
  2. The College of Chemistry, the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Wiejin Road 94#, Tianjin, 300071, P. R. China. [email protected].
  3. The College of Chemistry, the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Wiejin Road 94#, Tianjin, 300071, P. R. China. [email protected].
  4. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300071, P. R. China. [email protected].

PMID: 26946315 DOI: 10.1002/chem.201600248

Abstract

Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ-functionalized ketones with high to excellent yields. This reaction actually involved an intramolecular O-H insertion cyclization of an alkyne to form the dihydrofuran intermediate, which was followed by the nucleophilic addition ring-opening of a dihydrofuran to give the target compound.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: 1,5-enynols; cyclization; gold catalysis; hydration; nucleophilic substitution; ring-opening reactions

Publication Types