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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

Supporting Info

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, and Kissei Pharmaceutical Co., Ltd., Discovery Research, R & D, 4365-1, Kashiwabara, Hotaka, Minamiazumi, Nagano 399-8304, Japan

J. Org. Chem., 2001, 66 (4), pp 1200–1204

DOI: 10.1021/jo0014921

Publication Date (Web): January 30, 2001

To whom correspondences should be addressed. Tel.: +81-424-95-8764. Fax: +81-424-95-8763.

†

Meiji Pharmaceutical University.

‡

Kissei Pharmaceutical Co., Ltd.

, kawasaki@my-pharm.ac.jp

Abstract

The reverse aromatic Cope rearrangement of 2-allyl-3-alkylideneindolines obtained by Horner−Wadsworth−Emmons olefination of 2-allylindolin-3-ones was performed. 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. The aromatization as a new driving force in the Cope rearrangement is preferable to the conjugation with the carbonyl and cyano groups and also to the alkyl substitution pattern, which are well-known driving forces.

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