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Preference of 4-exo Ring Closure in Copper-Catalyzed Intramolecular Coupling of Vinyl Bromides with Alcohols

Yewen Fang and Chaozhong Li*

*Joint Laboratory of Green Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China, Email: cligmail.sioc.ac.cn

Y. Fang, C. Li, J. Am. Chem. Soc., 2007, 129, 8092-8093.

DOI: 10.1021/ja072793w (free Supporting Information)


Abstract

The intramolecular O-vinylation of γ-bromohomoallylic alcohols with 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand in refluxing MeCN led to the convenient formation of the corresponding 2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. 4-exo cyclization is preferred over other modes of cyclization.


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Preference of β-Lactam Formation in Cu(I)-Catalyzed Intramolecular Coupling of Amides with Vinyl Bromides

Q. Zhao, C. Li, Org. Lett., 2008, 10, 4037-4040.

"Ligand-Free" CuI-Catalyzed Highly Efficient Intramolecular S-Vinylation of Thiols with Vinyl Chlorides and Bromides

Q. Zhao, L. Li, Y. Fang, D. Sun, C. Li, J. Org. Chem., 2009, 74, 459-462.


Key Words

Ullmann Synthesis, Cyclic Ethers, Oxetanes


ID: J48-Y2007-2110