拡張可能な天然製品合成のための多機能オーガノボロン化合物
Fanke Meng1, Kevin P McGrath1, Amir H Hoveyda1
1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Nature
|September 19, 2014
まとめ
この研究は,高度な選択性を持つ複雑な分子を作成するための新しい触媒プロセスを導入しています. この方法は,安価な銅触媒と温和な条件を用いて,炭素-炭素結合と三置換アルケンを効率的に形成します.
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:
- エナチオセレクティブC-C結合形成とダイアステロセレクティブ三置換アルケンの合成は,有機化学において極めて重要です.
- これらの変換を費用対効果の高い触媒と穏やかな条件で同時に達成することは非常に望ましい.
研究 の 目的:
- エナチオセレクティブおよびダイアステロセレクティブ合成のための容易な多成分触媒プロセスを開発する.
- ステレオジェニックセンター,単位置換アルケーン,機能化可能なアルケニルボロン群を備えた貴重な中間物質を作成する.
主な方法:
- モノ置換されたアレンに銅-ボロン添加,その後アリル置換.
- ヘテロサイクリック塩から派生した頑丈で簡単に作製できる銅基触媒を使用しています.
主要な成果:
- 優れた選択性 (>98%の分枝およびステレオ選択性) とエナティオメール比率 (>99:1) を有する高収量 (最大89%) を達成しました.
- 製品にはステレオジェニックな炭素,単位置換アルケーン,Z-三位置換アルケニルボロン成分が含まれています.
- 自然産物ロットネストールとハーボキシジエンのグラムスケールのエナチオセレクティブ合成による有用性が実証されています.
結論:
- 開発された多成分触媒プロセスは,複雑な有機分子への効率的で選択的な経路を提供します.
- 安価で頑丈な銅触媒は,穏やかな環境下での実用的な合成を可能にします.
- この方法論は,天然製品やその他の複雑な標的のエナチオセレクティブ合成のための貴重なツールを提供します.
さらに関連する動画
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
8.5K
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
6.0K
関連する概念動画
03:08Hydroboration-Oxidation of Alkenes
9.8K
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.
9.8K
02:36Regioselectivity and Stereochemistry of Hydroboration
7.7K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
7.7K
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
19.7K
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.
19.7K
02:15Preparation of Alcohols via Addition Reactions
5.7K
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...
5.7K
01:25Production of Organic Acids
105
Lactic acid, an important organic acid extensively applied in food, pharmaceutical, and biodegradable polymer industries, is primarily produced via microbial fermentation. This method is favored over chemical synthesis due to its environmental sustainability and capacity for enantiomerically pure product formation. Among various microbial processes, the fermentation of starch-based substrates stands out due to the abundance and renewability of raw materials like corn and potatoes.Hydrolysis of...
105
01:18Production of Biopesticides
97
Biopesticides offer a sustainable alternative to chemical pesticides, utilizing microbial agents to control agricultural pests. Bacillus thuringiensis (Bt) is a widely employed bacterium known for its potent insecticidal activity. Bt biopesticides are favored for their specificity to insect pests, minimal environmental impact, and natural degradability.Mechanism of Bt Toxin Action Bt produces insecticidal crystal (Cry) proteins during its sporulation phase. These proteins form parasporal...
97