Reverse Aromatic Cope Rearrangement of 2-Allyl-3-alkylideneindolines Driven by Olefination of 2-Allylindolin-3-ones: Synthesis of α-Allyl-3-indole Acetate Derivatives
Tomomi Kawasaki,* Yoshinori Nonaka, Kazuaki Watanabe, Atsuyo Ogawa, Kazuhiro Higuchi, Romi Terashima, Kouhei Masuda, and Masanori Sakamoto
*Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo 204-8688, Japan, Email: kawasakimy-pharm.ac.jp
T. Kawasaki, Y. Nonaka, K. Watanabe, A. Ogawa, K. Higuchi, R. Terashima, K. Masuda, M. Sakamoto, J. Org. Chem., 2001, 66, 1200-1204.
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A reverse aromatic Cope rearrangement of 2-allyl-3-alkylideneindolines obtained by Horner-Wadsworth-Emmons olefination of 2-allylindolin-3-ones with diethyl cyanomethylphosphonate provided α-allyl-3-indole acetonitriles. When 2-allylindolin-3-ones were treated with phosphonium ylides in refluxing toluene, domino Wittig reaction and reverse aromatic Cope rearrangement took place to give α-allyl-3-indole acetate derivatives in good yields.
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Wittig-Horner Reaction, Wittig Reaction, Cope Rearrangement, Indoles