"常温でも分離可能なアミド配座異性体の構造特性：
書誌事項
- タイトル別名
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- Structural Property of Separable Amide Rotamers: Isomerization through the Formation of the Lithium Enolate.
説明
2,4,6-Tri-tert-butyl anilide derivatives are unique compounds which can be isolated rotational isomers based on amide bond at rt. Recently, we succeeded in the highly selective stereodivergent synthesis of E- and Z-rotamers of these anilide derivatives using Pd chemistry. We report here on the novel structural property of 2,4,6-tri-tert-butylanilide. Namely, interconversion between the separable 2,4,6-tri-tert-butylanilide rotamers was found to easily occur at rt through formation of the lithium enolate. Protonation of the anilide enolate gave the anilide rotamer mixture of E-major. On the other hand, reactions of lithium enolate prepared from 2,4,6-tri-tert-butylpropionanilide with alkyl bromides preferentially afforded a Z-rotamer of alkylated products. In particular, n-propylation with the enolate from E-rotamer occurred with almost complete inversion of the rotational isomerism.
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 37 (0), 56-56, 2011
日本薬学会化学系薬学部会
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キーワード
詳細情報 詳細情報について
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- CRID
- 1390001205633502464
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- NII論文ID
- 130006995605
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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
