Synthesis of monocyclic nine-membered compounds by the [4+3+2] cycloaddition-bond cleavage strategy

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• 作者：Ryu Yamasaki ; Korehito Kato ; Daichi Hanitani ; Yuichiro Mutoh ; Shinichi Saito ; ^{ssaito@rs.kagu.tus.ac.jp}
• 关键词：Cycloaddition ; Medium-sized ring ; Hydroxylamine ; Reductive cleavage ; Nickel catalyst ; N&ndash ; O bond clevage ; Nine-Membered Carbocycle
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：3 July, 2013
• 年：2013
• 卷：54
• 期：27
• 页码：3507-3509
• 全文大小：920 K

文摘

Monocyclic nine-membered compounds were synthesized by the cleavage of the six-membered ring of the bicyclic compounds. Thus, the bicyclic compounds which consist of six- and nine-membered rings were synthesized by the Ni-catalyzed [4+3+2] cycloaddition, and the cleavage of the N-O bond, which was incorporated in the six-membered ring, proceeded in the presence of Mo(CO)₆ to yield the monocyclic compound. On the other hand, the cleavage of the C-O bond proceeded efficiently in the presence of SmI₂.