Pd触媒と有機ホウ素試薬を用いたアレニルアルデヒドの環化カップリング反応
書誌事項
- タイトル別名
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- Palladium-Catalyzed Cyclization of Allenyl Aldehyde with Organoboronic Reagents
抄録
We have developed an efficient synthetic method for 3-substituted-3-cyclohexenols and -cyclopentenol based on Pd(0)-catalyzed alkylative, arylative, alkenylative, alkynylative, and borative cyclization reaction of allene-carbonyl compounds. Microwave irradiation increases not only the reaction rate but also the product yield by suppressing formation of hydroarylation byproducts observed in the same catalytic system. Cyclization of optically active 1,3-disubstitted allene-aldehyde reveals that the reaction proceeds through not carbopalladation but 'anti-Wacker'-type oxidative addition.<BR>However, this catalytic system was unsuitable for the cyclization of 5,6-dienal and provided five-membered cyclic alcohols in poor yield and selectivity. A catalyst screening effort disclosed that diphosphine-ligand Pd(II) catalyzed the arylative cyclization of 5,6-dienals to provide cis-fused five-membered cyclic homoallylic alcohols in high yield.
収録刊行物
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- 反応と合成の進歩シンポジウム 発表要旨概要
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反応と合成の進歩シンポジウム 発表要旨概要 33 (0), 117-117, 2007
日本薬学会化学系薬学部会
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詳細情報 詳細情報について
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- CRID
- 1390001205633908480
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- NII論文ID
- 130006996082
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可