有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
γ-メチリデン-δ-バレロラクトン:パラジウム触媒による分子間環化反応における新規反応剤
新谷  亮
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2010 年 68 巻 8 号 p. 834-844

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Intermolecular cycloadditions catalyzed by transition-metal complexes are powerful methods for convergent synthesis of cyclic materials. In this context, we recently devised γ-methylidene-δ-valerolactones as new reagents for intermolecular decarboxylative cyclization reactions with several reaction partners to produce various cyclic compounds under palladium catalysis. These lactones effectively serve as precursors for 1,4-zwitterionic species through oxidative addition to palladium(0) and successive decarboxylation, thereby introducing a four-carbon unit in a newly formed cyclic framework. In some cases, however, they provide three carbons in a cyclic framework with a spirocyclopropane moiety. Herein we describe an overview of the reactions using these lactones, including some asymmetric variants as well as mechanistic insights for these decarboxylative cyclization reactions.

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© 2010 社団法人 有機合成化学協会
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