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A New Strategy for Construction of Eight-Membered Carbocycles by Brook Rearrangement Mediated [6 + 2] Annulation

Kei Takeda,* Hidekazu Haraguchi and Yasushi Okamoto

*Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan, Email:

K. Takeda, H. Haraguchi, Y. Okamoto, Org. Lett., 2003, 5, 3705-3707.

DOI: 10.1021/ol0353767

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A [6 + 2] annulation that involves the combination of β-alkenoyl acylsilanes and a vinyllithium derivative enables in one operation and a stereoselective manner the construction of eight-membered ring systems containing useful functionalities for further synthetic elaboration from readily available six- and two-carbon components.

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proposed mechanisms

Key Words

Brook Rearrangement, Cyclic Ketones, Cyclobutanols, Cyclopentanols

ID: J54-Y2003-2180