書誌事項
- タイトル別名
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- (3,3)Sigmatropic Ring Expansion of Cyclic Thionocarbonates of Medium Ring-Size.
- チュウ カンジョウ チオノカルボナート ノ 3 3 シグマトロピー テンイ オ
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抄録
A highly stereoselective synthesis of (Z) - or (E) -double bonds in 10-membered thiolcarbonates is achieved by the [3, 3] sigmatropic rearrangement of 8-membered thionocarbonates which proceeds through the chairlike vs. boatlike transition states. The formation of the 8-membered intermediates followed by their [3, 3] sigmatropic rearrangements were investigated by experiments and theoretical calculations. Their utilities of this methodology have been demonstrated by the unique and stereoselective synthesis of (-)-yellow scale pheromone. Moreover, medium-membered heterocyclic allenes were synthesized by this method. The structure and reactivity of a new type of strained 8-membered allene were also examined. Using this method combined with a novel application of the newly developed SmI2-HMPA reduction of the cyclic allene, the antifungal constituent of a Sapium japonicum was synthesized.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 53 (8), 712-723, 1995
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205277465728
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- NII論文ID
- 10001714844
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DyaK2MXnsFOhtL8%3D
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 3628051
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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
- NDL
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- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可