マグネシウムカルベノイドの転位反応を鍵反応とする共役エンイン化合物の新規合成法
書誌事項
- タイトル別名
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- Synthesis of conjugated enynes by magnesiumcarbenoid 1,2-CC insertion as the key reaction
説明
The reaction of 1-chlorovinyl p-tolyl sulfoxides, which were derived from ketones and chloromethyl p-tolyl sulfoxide, with lithium acetylides gave adducts in moderate to good yields. Treatment of the adducts with Grignard reagents resulted in the formation of magnesium carbenoids by the sulfoxide-magnesium exchange reaction. 1,2-Carbon–carbon insertion (1,2-CC insertion) reaction of the generated magnesium carbenoids took place to afford conjugated enynes in good to high yields. Starting there reactions from unsymmetrical ketones, the 1,2-CC insertion was proved to be stereospecific. Furthermores the reaction of 1-chlorovinyl p-tolyl sulfoxides, which were derived from aldehydes, with lithium acetylides gave conjugated enynes via 1,2-Carbon–hydrogen insertion (1,2-CH insertion) reaction of the generated lithium carbenoids inermediates. This procedure provides a good method for the synthesis of multi-substituted conjugated enynes.
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 36 (0), 12-12, 2010
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
- 1390282680612140928
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- NII論文ID
- 130006997906
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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
