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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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金で触媒化された三成分タンデムプロセス:アルキン,アミン,グリオキシル酸から複合ブテノリドを効率的かつ簡単に組み立てる
Qiang Zhang1, Ming Cheng, Xiaoyu Hu
1Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.
Journal of the American Chemical Society
|May 12, 2010
まとめ
新しい黄金触媒反応は,単純な起始材料から複雑なブテノリドを効率的に生成します. この3つのコンポーネントのタンデムプロセスは,1つのステップで複数の結合を形成し,さらなる化学的改変を可能にします.
科学分野:
- 有機化学 オーガニック・ケミストリー
- カタリシス カタリシス カタリシス
- 合成方法論 合成方法論
背景:
- ブテノリドは,多様な生物学的活動を持つ重要なヘテロサイクル化合物です.
- 高機能化されたブテノリドへの効率的な合成経路は,医薬品化学と材料科学において極めて重要です.
- 既存の方法は,多くの場合,複数のステップと厳しい条件を必要とします.
研究 の 目的:
- 機能化されたブテノリドを合成するための新しい,効率的で簡単な方法を開発する.
- 金で触媒化された3つのコンポーネントのタンデム反応を確立し,迅速なエスカフォードの組み立てを行う.
- さらに合成処理のために反応部位を持つブテノリド構造を作成する.
主な方法:
- アルキン,アミン,およびグリオキシル酸を含む1つのポット,3つの成分反応.
- 単一の黄金触媒を用いて,複数の結合形成とサイクロアイソメリゼーションを媒介する.
- 独占的なエンド選択性サイクロアイソメリゼーションを用いて,その後,電愛性トラッピングを行います.
主要な成果:
- 2種類の高度に機能化されたブテノリドの合成に成功した.
- 単一の触媒サイクルで4つ以上の化学結合の形成.
- 複雑なブテノリド基板の組み立ては,シンプルで,商業的に利用可能な出荷材料から.
結論:
- 開発された金触媒タンデムプロトコルは,価値あるブテノリド構造への効率的で汎用的な経路を提供します.
- この方法論は,複雑なヘテロサイクルのスキャフォルドの合成を大幅に簡素化します.
- その結果生じるブテノリドは,反応性のあるハンドルを有しており,有機合成における様々な下流応用を容易にする.
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02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
03:08Hydroboration-Oxidation of Alkenes
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
02:15Preparation of Alcohols via Addition Reactions
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
01:16Cycloaddition Reactions: Overview
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.