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- 黒澤 渉
- 味の素株式会社イノベーション研究所フロンティア研究所先端融合研究グループ
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- Roberts Paul M.
- オックスフォード大学化学科
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- Davies Stephen G.
- オックスフォード大学化学科
書誌事項
- タイトル別名
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- Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
- アンモニウムキ オ カイシタ カンジョウ アリルアミン ホモアリルアミン ノ サンカ
この論文をさがす
抄録
We have developed a metal-free and highly diastereoselective ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes upon treatment with Cl3CCO2H followed by mCPBA. The reaction mechanism involves protection of the amine by protonation, hydrogen-bonded delivery of the oxidant by the allylic ammonium ion formed in situ, followed by highly regioselective ring-opening of the intermediate syn-epoxide by trichloroacetic acid, to give a 1,2-anti-2,3-syn amino diol after deprotection. Meanwhile, oxidation of the corresponding tertiary amine N-oxide is entirely complementary and proceeds with high anti-diastereoselectivity to afford the corresponding 1,2-anti-2,3-anti amino diol after deprotection, consistent with the epoxidation reaction proceeding under steric or dipole control. The ammonium-directed oxidation protocol is general for a range of cyclic allylic and homoallylic amines and facilitates the metal-free synthesis of all four diastereoisomers of the corresponding 3-amino-1,2-diols, and has recently been employed as one of the key steps in the syntheses of (±)-1-deoxynojirimycin and (±)-1-deoxyaltronojirimycin.
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 68 (12), 1295-1306, 2010
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
- 1390001205312276096
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- NII論文ID
- 10027409621
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3cXhsFOgtbnM
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 10932784
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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